Aldehyde Reactant Patents (Class 568/433)
  • Patent number: 6127581
    Abstract: Fluorinated benzaldehydes are obtainable in a simple and inexpensive manner and in significantly improved yields when chlorinated benzaldehydes are reacted with alkali metal fluorides at temperatures in the range from about 130 to 200.degree. C. in the presence of less than about 2 mol % of quaternary phosphonium salts, based on chlorine atoms to be replaced, at initial concentrations of more than 2.5 mol of the chlorinated benzaldehydes per kg of dipolar aprotic solvent. Fluorinated benzaldehydes obtained in this way can advantageously be hydrogenated with hydrogen in the presence of noble metal catalysts to give fluorinated benzyl alcohols.
    Type: Grant
    Filed: August 6, 1999
    Date of Patent: October 3, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Wiedemann, Albrecht Marhold, Claus Dreisbach
  • Patent number: 6114587
    Abstract: The selective obtainment of .alpha.-alkyl cinnamaldehydes, such as Jasmine aldehyde is carried out by a process that involves two consecutive reactions: acetalization of an n-alkyl aldehyde by direct reaction with an alcohol or by transacetalization followed by the reaction between said acetal and aromatic aldehyde such as benzaldehyde using molecular sieves with regular pore distribution in the range of micro and mesopores and between 6 and 100 .ANG. as acid catalysts.
    Type: Grant
    Filed: February 2, 1999
    Date of Patent: September 5, 2000
    Assignees: Consejo Superior de Investigaciones Cientificas, Universidad Politeonica de Valencia
    Inventors: M.sup.a Jose Climent Olmedo, Rut Guil Lopez, Sara Iborra Chornet, Jaime Primo Millo, Avelino Corma Canos
  • Patent number: 6020531
    Abstract: A benzothiophene compound represented by a formula: ##STR1## wherein R.sup.1 represents a lower alkyl group, and R.sup.2 represents a halogen atom; a lower alkyl group; or a cycloalkyl group or cycloalkenyl group which may optionally be substituted with a lower alkyl group, a hydroxy group, an acyloxy group or an oxo group,which is a useful intermediate for synthesizing a 2-sub-stituted-3-(4-substituted benzoyl)-6-hydroxybenzo[b]-thiophene derivative having an antiestrogenic activity can be produced in an industrially advantageous manner by subjecting a compound represented by a formula: ##STR2## to a ring-closing reaction. Further, the novel compound of the formula (II) described above is a useful intermediate in the process of the present invention.
    Type: Grant
    Filed: January 25, 1999
    Date of Patent: February 1, 2000
    Assignee: Teikoku Hormone Mfg. Co., Ltd.
    Inventors: Masafumi Shiraiwa, Shuichiro Sato, Koji Doguchi
  • Patent number: 5856583
    Abstract: A method for the preparation of 2-hydroxyarylaldehydes from an aryloxy magnesium compound and formaldehyde, which comprises reacting at a temperature from 40.degree.-120.degree. C., an aryloxy magnesium compound having an aryloxy anion and a non-aryloxy anion and in which (a) the non-aryloxy anion is more basic than the aryloxy anion such that when the aryloxy magnesium compound is brought into contact with an acidic species, the acid reacts more preferentially with the non-aryloxy anion to form an aryloxy magnesium salt and (b) the aryloxy anion has at least one free position ortho to the hydroxyl group in the aryloxy anion, with formaldehyde or a compound capable of giving rise to formaldehyde under the reaction conditions in the presence of a polar co-solvent capable of providing the non-aryloxy anion in the aryloxy magnesium compound characterized in that the non-aryloxy anion is selected from the group consisting of an oxide, a hydroxide, a carboxylate, a sulphate and a nitrate.
    Type: Grant
    Filed: May 21, 1997
    Date of Patent: January 5, 1999
    Assignee: Allco Chemical Corp.
    Inventors: Jeffrey Howard Dimmit, Mark Alan Kearns, William H. Chambless
  • Patent number: 5786516
    Abstract: The present invention relates to a novel process for the preparation of isovanillin.The process for the preparation of isovanillin according to the invention is characterized in that it consists in dealkylation being carried out using a strong acid, selectively in the 3-position, on a 3-alkoxy-4-methoxybenzaldehyde wherein said alkoxy group has at least two carbon atoms.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: July 28, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventor: Christian Maliverney
  • Patent number: 5770762
    Abstract: Described is a process for producing a 4-substituted-2-butenal represented by the following formula (1); ##STR1## (wherein X represents an acyloxy group or halogen atom; R represents hydrogen atom, an aliphatic hydrocarbon group or an aromatic hydrocarbon group; and these hydrocarbon groups can be substituted with hydroxyl group, an alkoxy group, an aryloxy group, an acyl group or an alkoxycarbonyl group), which is useful as synthetic intermediates of phormaceutieals, agricultural chemicals and the like,comprising subjecting a substituted acetaldehyde represented by the following formula (2);X--CH.sub.2 --CHO (2)(wherein X has the same meaning as defined above), with an aldehyde represented by the following formula (3);R--CH.sub.2 --CHO (3)(wherein R has the same meaning as defined above) in the presence of an amino carboxylic acid.
    Type: Grant
    Filed: April 22, 1997
    Date of Patent: June 23, 1998
    Assignee: Kuraray Co., Ltd.
    Inventors: Hideharu Iwasaki, Takashi Onishi
  • Patent number: 5763675
    Abstract: A method for the preparation of a 2-hydroxyarylaldehyde which comprises reacting a magnesium bis-hydrocarbyloxide, derived at least in part from a hydroxyaromatic compound having at least one free position ortho to the hydroxyl group, with formaldehyde or a formaldehyde-liberating compound under substantially anhydrous conditions at a pressure of from 50 to 700 mm Hg absolute.
    Type: Grant
    Filed: January 5, 1996
    Date of Patent: June 9, 1998
    Assignee: Zeneca Limited
    Inventor: Daniel Levin
  • Patent number: 5756853
    Abstract: The subject of the present invention is a process for the preparation of a 4-hydroxybenzaldehyde carrying at least one substituent in the position ortho to the OH group.It more particularly relates to the preparation of 3-methoxy-4-hydroxybenzaldehyde and of 3-ethoxy-4-hydroxybenzaldehyde.The process for the preparation of a substituted 4-hydroxybenzaldlehyde, substituted at least in the 3 position by an alkoxy group, is characterized in that it comprises subjecting a substituted phenol compound, substituted at least in the 2 position by an alkoxy group and in which the 4 and 6 positions are free, to a first stage of carboxylation in the 6 position, then to a stage of hydroxymethylation in the 4 position, followed by a stage of oxidation of the hydroxymethyl group to a formyl group, and finally to a last decarboxylation stage.
    Type: Grant
    Filed: October 16, 1996
    Date of Patent: May 26, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Pascal Metivier, Isabelle Jouve, Christian Maliverney
  • Patent number: 5728892
    Abstract: The invention relates to a method for preparing an .alpha.-alkylcinnamaldehyde via aldol concensation of a benzaldehyde and an alkanal, with pyrrolidine being employed as a catalyst. The method is suitable, in particular, for preparing .alpha.-hexylcinnamaldehyde by aldol condensation of benzaldehyde and n-octanal, in particular for preparing .alpha.-hexylcinnamaldehyde of olfactory quality, since it was found that, in the method according to the invention, relatively little .alpha.-hexyldecenal, the aldol condensation product of n-octanal, is formed. Preferably, the aldol condensation is carried out without a solvent in the presence of an acid, and the alkanal is metered in over time to a mixture which contains pyrrolidine and benzaldehyde.
    Type: Grant
    Filed: November 6, 1996
    Date of Patent: March 17, 1998
    Assignee: DSM N.V.
    Inventors: Alie Kuiterman, Hubertus J. A. Dielemans, Richard Green, Anna M. C. F. Castelijns
  • Patent number: 5703269
    Abstract: The preparation of aromatic olefins from haloaromatics and olefins (Heck reaction) is carried out in the presence of palladium complexes as catalysts, which complexes contain heterocyclic carbenes as ligands.
    Type: Grant
    Filed: December 29, 1995
    Date of Patent: December 30, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang A. Herrmann, Jakob Fischer, Martina Elison, Christian Kocher
  • Patent number: 5648552
    Abstract: The present invention relates to a novel process for the preparation of isovanillin.The process for the preparation of isovanillin according to the invention is characterized in that it consists in dealkylation being carried out using a strong acid, selectively in the 3-position, on a 3-alkoxy-4-methoxybenzaldehyde wherein said alkoxy group has at least two carbon atoms.
    Type: Grant
    Filed: October 23, 1995
    Date of Patent: July 15, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventor: Christian Maliverney
  • Patent number: 5502257
    Abstract: Disclosed is a process for the preparation of cyclopropanecarboxaldehyde by the thermal isomerization of 2,3-dihydrofuran under superatmospheric pressure, e.g., at a temperature of about 300.degree. to 600.degree. C. and a pressure of about 3 to 345 bars absolute.
    Type: Grant
    Filed: February 21, 1995
    Date of Patent: March 26, 1996
    Assignee: Eastman Chemical Company
    Inventors: Shaowo Liang, Timothy W. Price, Timothy R. Nolen, Daniel B. Compton, David C. Attride
  • Patent number: 5457239
    Abstract: A process for the preparation of a formylated aromatic compound comprising contacting an aromatic compound with (i) a halogenated compound in the presence of a Lewis acid, and (ii) a base, is described. The subject process provides an efficient and effective means of preparing formylated compounds which may be useful in a wide variety of applications.
    Type: Grant
    Filed: May 25, 1994
    Date of Patent: October 10, 1995
    Assignee: Union Camp Corporation
    Inventors: Walter C. Frank, Richard L. Veazey, John J. Mahurter, Mark J. Jenkins, Neil R. Fairfax
  • Patent number: 5434302
    Abstract: The present process is directed to preparing optically active 2-aryl alkyl aldehydes by various processes through the use of an optically active amine, (-)-2'-amino-3-phenyl propane. The aldehyde formed can then be oxidized to produce the corresponding acid.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: July 18, 1995
    Inventor: H. Henrich Paradies
  • Patent number: 5430194
    Abstract: The present invention relates to a process for producing an optically active aldehyde (first aldehyde) containing a reduced amount of the corresponding enantiomeric aldehyde (second aldehyde) which process comprises: (1) providing an initial solution containing a non-eutectic mixture of the first aldehyde and the second aldehyde, which mixture has a composition in the compositional region where only the first aldehyde crystallizes when its solubility limit in the solution is exceeded, and (2) maintaining the solution at a temperature above the eutectic temperature of the mixture and under conditions such that the solubility limit of the first aldehyde is exceeded so as to form a crystalline first aldehyde containing relatively less of the second aldehyde than was present in the initial solution.
    Type: Grant
    Filed: June 24, 1994
    Date of Patent: July 4, 1995
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Bruce A. Barner, John R. Briggs, Jonathan J. Kurland, Charles G. Moyers, Jr.
  • Patent number: 5382694
    Abstract: A process for the continuous production of aromatic aldehydes of the formula (1) ##STR1## in which Ar is an aryl radical, R.sup.1, R.sup.2 and R.sup.3 independently of one another are hydrogen, fluorine, chlorine or bromine atoms, in which dichloromethyl-substituted aromatics of the formula (2) ##STR2## in which Ar, R.sup.1, R.sup.2, R.sup.3 have the above meanings, are continuously hydrolyzed with an aqueous solution of one or more catalysts of the formula (3)MX.sub.n (3)in which M is a transition metal selected from the group comprising iron, nickel, copper, chromium, thallium, zinc and mercury, X is F, Cl, Br, I, OH, SO.sub.4, PO.sub.4 or NO.sub.3, and n depending on the oxidation state of the transition metal M is the number 1, 2, 3 or 4, in a concentration of from about 1 to about 50%, based on the weight of water in the catalyst solution, at temperatures of from about 70.degree. to about 160.degree. C.
    Type: Grant
    Filed: November 23, 1993
    Date of Patent: January 17, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gilbert Billeb, Georg Folz
  • Patent number: 5354915
    Abstract: This invention provides an improved process for converting .alpha.,.beta.-olefinically unsaturated aldehydic or ketonic compounds into the corresponding allylic alcohol using an alcohol as a hydrogen donor. This process is conducted in the presence of a supported tetragonal zirconium oxide catalyst or supported HfO.sub.2, V.sub.2 O.sub.5, NbO.sub.5, TiO.sub.2 and Ta.sub.2 O.sub.5 catalysts.
    Type: Grant
    Filed: December 21, 1992
    Date of Patent: October 11, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Walter T. Reichle
  • Patent number: 5354920
    Abstract: A method for the preparation of a 2-hydroxyarylaldehyde which comprises reacting an aryloxymagnesium halide derived from a phenol having at least one free ortho position relative to the phenolic hydroxy group with formaldehyde or a formaldehyde-liberating compound under substantially anhydrous conditions in the presence of a polar organic solvent other than hexamethylphosphoramide or 1,3-dimethyl-3,4,5,6-2(1H)-pyrimidone.
    Type: Grant
    Filed: August 10, 1993
    Date of Patent: October 11, 1994
    Assignee: Zeneca Limited
    Inventors: Brian G. Cox, Daniel Levin
  • Patent number: 5321165
    Abstract: A method of producing an ethynyl aromatic aldehyde comprises reacting a protected copper(I) acetylide salt with a halogen substituted aromatic compound to produce a protected ethynyl aromatic aldehyde.The protected ethynyl aromatic aldehyde may be deprotected to yield an acetylene terminated aromatic aldehyde which is useful for making acetylenic Schiff's base monomers and conductive polymers thereof.
    Type: Grant
    Filed: June 14, 1993
    Date of Patent: June 14, 1994
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Thomas DiBerardino, Patricia M. Lutz, Barbara F. Howell
  • Patent number: 5319142
    Abstract: An arylisonitrosoalkanone is hydrogenated in the presence of a noble metal catalyst and a weak carboxylic acid to form an arylalkanolamine which is then hydrogenated in the presence of a strong mineral acid and the transition metal catalyst to form an arylalkylamine. When the arylisonitrosoalkanone is an isonitrosoacetophenone, the isonitrosoacetophenone is prepared by one of two methods.In the first method, a substituted or an unsubstituted isonitrosoacetophenone is prepared from a corresponding substituted or unsubstituted acetophenone by oxidizing the acetophenone to form a substituted or an unsubstituted phenylglyoxalacetal in a reactor, hydrolyzing the phenylglyoxal acetal in the same reactor to form a corresponding substituted or unsubstituted phenylglyoxal, and condensing the phenylglyoxal with hydroxylamine or a salt thereof in the same reactor to form the substituted or unsubstituted isonitrosoacetophenone.
    Type: Grant
    Filed: October 6, 1992
    Date of Patent: June 7, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Joseph A. McDonough, Ahmed M. Tafesh, Olan S. Fruchey
  • Patent number: 5304685
    Abstract: A process for preparing 3-(hydroxyphenyl)propionaldehydes of the formula I ##STR1## and, where appropriate, for preparing 3-(hydroxyphenyl)propanols of the formula II ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl or C.sub.5 -C.sub.20 -alkylcycloalkylalkyl,R.sup.3 and R.sup.4 are each aryl, C.sub.7 -C.sub.20 -aralkyl, heterocycloalkyl or C.sub.3 -C.sub.20 -heterocycloalkylalkyl, entailsa) reacting phenols of the formula III ##STR3## where R.sup.1 and R.sup.2 have the abovementioned meanings, with 3-hydroxypropionaldehydes of the formula IV ##STR4## where R.sup.3 and R.sup.4 have the abovementioned meanings, in the presence of a basic catalyst at from 90.degree. to 230.degree. C. and under from 0.01 to 50 bar and, where appropriate,b) treating the resulting 3-(hydroxyphenyl)propionaldehydes of the formula I ##STR5## where R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: March 26, 1993
    Date of Patent: April 19, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Martin Schmidt-Radde
  • Patent number: 5292894
    Abstract: A process for the preparation of benzo[b]thiophenes of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 independently denote hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, nitro, cyano, halo, C.sub.1 -C.sub.4 alkylcarbonyl, benzoyl, C.sub.1 -C.sub.4 alkylcarbonylamino, benzoylamino,N-(C.sub.1 -C.sub.4 alkyl)phenylamino, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, phenylsulfonyl, aminosulfonyl, aminocarbonyl, C.sub.1 -C.sub.4 phenylalkyl and nitrobenzyl or R.sup.1 +R.sup.2 or R.sup.2 +R.sup.3 or R.sup.3 +R.sup.4 denote a butadienediyl chain optionally substituted by R.sup.1 to R.sup.4, in whicha) thiophenols of the general formula II ##STR2## in which the substituents R.sup.1 to R.sup.4 have the aforementioned meanings, are reacted with chloroacetaldehyde at a temperature ranging from 0.degree. to 150.degree. C. andb) the resulting (arylthio)acetaldehydes of the general formula III ##STR3## in which the substituents R.sup.
    Type: Grant
    Filed: February 17, 1993
    Date of Patent: March 8, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ebel, Juergen Schroeder
  • Patent number: 5260487
    Abstract: A method for the preparation of a 2-hydroxyarylaldehyde which comprises reacting a magnesium bis-hydrocarbyloxide derived at least in part from a hydroxyaromatic compound having at least one free position ortho to the hydroxyl group with formaldehyde or formaldehyde-liberating compound under substantially anhydrous conditions.
    Type: Grant
    Filed: August 19, 1992
    Date of Patent: November 9, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventor: Daniel Levin
  • Patent number: 5256826
    Abstract: A process for the preparation of aromatic carbonyl or sulfonyl compounds with a diaryl ether structure by reacting phenols with halogenated carbonyl- or sulfonylaromatic compounds in a dipolar aprotic solvent is carried out in the presence of catalytic amounts of alkali metal nitrite or an aromatic nitro, nitroso, azo, azoxy or hydrazo compound.
    Type: Grant
    Filed: August 31, 1992
    Date of Patent: October 26, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Erwin Hahn, Heinrich J. Eilingsfeld, Helmut Reichelt, Alexander Aumueller, Bernd Hupfeld
  • Patent number: 5254726
    Abstract: A method for synthesizing no-carrier-added (NCA) aryl [.sup.18 F] fluoride substituted aromatic aldehyde compositions bearing an electron donating group is described. The method of the present invention includes the step of reacting aromatic nitro aldehydes having a suitably protected hydroxyl substitutent on an electron rich ring. The reaction isThe U.S. Government has rights in this invention pursuant to Contract Number DE-AC02-76CH00016, between the U.S. Department of Energy and Associated Universities Inc.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: October 19, 1993
    Assignee: The United States of America as represented by the Department of Energy
    Inventors: Yu-Shin Ding, Joanna S. Fowler, Alfred P. Wolf
  • Patent number: 5227531
    Abstract: A process for the production of fluorobenzaldehydes which comprises reacting a chlorobenzaldehyde with an alkali fluoride in a dipolar aprotic medium.
    Type: Grant
    Filed: June 5, 1991
    Date of Patent: July 13, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans J. Metz, Klaus Warning
  • Patent number: 5198571
    Abstract: A region-specific monofunctionalization of a phenolic hydroxy onto a polyphenol for the preparation of a compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, --CN, formyl, carboxy, alkoxy carbonyl of up to 9 carbon atoms, aralkoxy carbonyl or up to 12 carbon atoms and halogen and R' is a hydroxy protective group comprising reacting a polyphenol of the formula ##STR2## wherein R has the above definition with a base to form the corresponding dianion, reacting the latter with a trialkyl borate of the formulaB(OAlk).sub.3wherein Alk is alkyl of 1 to 6 carbon atoms to form a compound of the formula ##STR3## reacting the latter with a reagent capable of introducing a hydroxy protective group and reacting the latter with a hydrolysis agent for the oxygen-boron bond to obtain the corresponding compound of Formula I.
    Type: Grant
    Filed: December 16, 1991
    Date of Patent: March 30, 1993
    Assignee: Roussel Uclaf
    Inventors: Jean-Louis Brayer, Daniel Calvo, Francois Ottello
  • Patent number: 5159117
    Abstract: A process for preparing .alpha.,.alpha.-dialkoxy ketones of the formula I ##STR1## where R.sup.1 and R.sup.2 are each, independently of one another, hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.30 -cycloalkylakyl, C.sub.9 -C.sub.30 -alkylcycloalkyl, unsubstituted or C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy-, halogen-, C.sub.1 -C.sub.4 -haloalkyl-, C.sub.1 -C.sub.4 -haloalkoxy-, phenyl-, phenoxy-, halophenyl-, halophenoxy- and/or cyano-substituted aryl, C.sub.7 -C.sub.20 -aralkyl or heterocyclyl,R.sup.2 is also ##STR2## R.sup.3 and R.sup.4 are each, independently of one another, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, aryl, C.sub.7 -C.sub.20 -arylalkyl, or together are an unsubstituted or C.sub.1-C.sub.4 -alkyl- substituted C.sub.2 -C.sub.7 -alkylene chain andR.sup.5 is R.sup.1 or together with R.sup.1 is an unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted C.sub.2 -C.sub.
    Type: Grant
    Filed: August 20, 1991
    Date of Patent: October 27, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Wegner, Stefan Karbach, Hubert Smuda, Eckhard Hickmann, Reiner Kober, Rainer Seele, Thomas Zierke
  • Patent number: 5130493
    Abstract: o-Hydroxy-benzaldehydes can be obtained by oxidation of the o-cresols, on which they are based, with oxygen in the presence of substances having a base reaction in a solvent if chelate complexes of iron, manganese or a mixuture of both with polyaza-macrocycles as chelating agents are employed as catalysts. Copper or a copper compound is advantageously added as a co-catalyst.
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: July 14, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albert Schnatterer, Helmut Fiege, Karl-Heinz Neumann
  • Patent number: 5117002
    Abstract: A process for the production of diaryl ethers which comprises heating, to a temperature of 80.degree. C. to 220.degree. C., a compound of the formula ##STR1## wherein X and Y are selected from the group consisting of H, CN, CO.sub.2 H, CHO, NO.sub.2, and CF.sub.3, provided that both X and Y may not simultaneously be H, in a solvent, in the presence of an inorganic base selected from the group consisting of the alkali metal carbonates, bicarbonates, and hydroxides, and in the presence of a catalyst selected from the group consisting of benzoic acid, substituted benzoic acids, C2-C4 aliphatic carboxylic acids, and alkali metal salts of said acids.
    Type: Grant
    Filed: January 14, 1991
    Date of Patent: May 26, 1992
    Assignee: Occidental Chemical Corporation
    Inventors: Robert A. Buchanan, Jeffrey S. Stults
  • Patent number: 5055621
    Abstract: .alpha.-cinnamic aldehydes especially amyl and hexyl cinnamic aldehydes, are prepared by aldol condensation using a glycol solvent especially diethylene glycol.
    Type: Grant
    Filed: April 11, 1990
    Date of Patent: October 8, 1991
    Assignee: Unilever Patent Holdings B.V.
    Inventor: Laurence S. Payne
  • Patent number: 5041604
    Abstract: A process for producing a high quality di(aryloxy)alkane with a high yield by the use of readily commercially available materials, without using any particular solvent or agent and by means of a simple operation and a general apparatus is provided, which process comprises subjecting a halogenated alkane of the formula (II)X--A--Y (II)wherein X and Y each represent a halogen atom and A represents a lower alkylene group, and a phenol of the formula (III) ##STR1## wherein R.sub.1 to R.sub.5 each are same or different, represent hydrogen, halogen, lower alkyl, lower alkoxy, carboxylic acid salt, acyl or nitro group, and may form a ring in conjunction of two adjacent groups,to condensation reaction in the presence of an alkali in an aqueous medium to form a di(aryloxy)alkane of the formula (I) ##STR2## and is characterized (i) by carrying out the condensation reaction in a molar ratio of the compound of the formula (II): the phenol of the formula (III): the alkali in terms of monovalent base of 1:1.5 to 3.0:1.
    Type: Grant
    Filed: June 20, 1990
    Date of Patent: August 20, 1991
    Assignee: Sanko Kaihatsu Kagaku Kenkyusho
    Inventors: Toranosuke Saito, Masakatu Kitani, Takashi Ishibashi
  • Patent number: 5026919
    Abstract: Basic intermediate or large pore zeolites having a Constraint Index less than 12 are useful as catalysts in the dehydrogenation-aromatization of cyclie dienes, in the isomerization of olefins and in the aldol condensation, and particularly in the cyclization of acetonylacetone to 3-methyl-2-cyclopenten-1-one.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: June 25, 1991
    Assignee: Mobil Oil Corporation
    Inventor: Ralph M. Dessau
  • Patent number: 4967013
    Abstract: Hydroxybenzaldehydes of the formula (I) are prepared from a benzaldehyde of the formula (II) or its acetal, in which R.sup.1 in the R.sup.1 O-phenyl ether group is an alkyl, cycloalkyl, alkylcycloalkyl or alkylaryl radical, R.sup.2 is H or OH or is identical to R.sup.1 and one or more R.sup.1 O-phenyl ether groups are ortho, meta or para to the aldehyde function, by a process in which a benzaldehyde of the formula (II) or its acetal, in which R.sup.1 and R.sup.2 have the abovementioned meanings and one or more R.sup.1 O-phenyl ether groups occupy the abovementioned position with respect to the aldehyde function, is converted into a hydroxybenzaldehyde of the formula (I) in the presence of water over a zeolite as a heterogeneous catalyst. ##STR1## The catalysts used are, in particular, zeolites of the pentasil type.
    Type: Grant
    Filed: May 3, 1989
    Date of Patent: October 30, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Steck, Helmut Lermer, Harald Rust, Gerhard Fritz, Hardo Siegel
  • Patent number: 4945186
    Abstract: A method of producing 3-bromobenzaldehyde is disclosed, wherein, upon producing 3-bromobenzaldehyde by allowing benzaldehyde to react with bromine in the presence of brominating catalyst in 1,2-dichloroethane being a reaction solvent, 1,2-dichloroethane having been used for aforesaid reaction as a reaction solvent is recovered and, after the recovered solvent is allowed first to react with chlorine in the presence of above brominating catalyst, the reaction is performed by the addition of benzaldehyde and bromine. Foregoing 1,2-dichloroethane recovered may be brought to the reaction with chlorine with or without adding fresh 1,2-dichloroethane and above brominating catalyst is preferably aluminum chloride.
    Type: Grant
    Filed: January 2, 1990
    Date of Patent: July 31, 1990
    Assignee: Toso Organic Chemical Co., Ltd.
    Inventors: Shinichi Matsuura, Osamu Miyano
  • Patent number: 4933498
    Abstract: 3,4,5-Trialkoxybenzaldehydes, notably 3,4,5-triamethoxybenzaldehyde, are prepared by hydrolyzing 5-bromo-4-hydroxy-3-methoxybenzaldehyde with an alkali metal hydroxide, in water and in the presence of a copper catalyst, and then directly sequentially (i.e., without separating any reaction intermediates) etherifying the 4,5-dihydroxy-3-methoxybenzaldehyde thus produced with a lower alkyl halide, in an aqueous medium and at a pH maintained at a value of from 6 to 12, optionally in the presence of a catalyst.
    Type: Grant
    Filed: August 7, 1989
    Date of Patent: June 12, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventor: Michel Crochemore
  • Patent number: 4914243
    Abstract: Process for the production of 2-alkoxy or aryl(lower)alkoxy-6-methoxy-1-naphthalenecarboxaldehyde chemical intermediates by demethylating 2,6-dimethoxy-1-naphthalenecarboxaldehyde with a nucleophilic sulfide reagent at the 2-position and reacting the resulting phenolate salt with an alkylating reagent. Said aldehydes are themselves intermediates for the manufacture of compounds which inhibit aldose reductase and are useful for the treatment of diabetic complications.
    Type: Grant
    Filed: April 27, 1989
    Date of Patent: April 3, 1990
    Assignee: American Home Products Corporation
    Inventor: John G. Bauman
  • Patent number: 4866197
    Abstract: Process for the production of N-[[2-alkoxy-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-meth ylglycine esters and intermediates for their production. Said esters are themselves intermediates for the manufacture of compounds which inhibit aldose reductase and are useful for the treatment of diabetic complications.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: September 12, 1989
    Assignee: American Home Products Corporation
    Inventor: John G. Bauman
  • Patent number: 4849546
    Abstract: A multi-step process for the preparation of ethynylbenzaldehydes from bromo- or iodobenzaldehydes is disclosed. The arylhalogen is replaced with a protected ethynyl compound which is subsequently cleaved by base to form the arylacetylene. The aldehydic functionlity is preserved by formation of a corresponding Schiff's base or acetal, and its subsequent regeneration by treatment with aqueous acid.
    Type: Grant
    Filed: May 9, 1988
    Date of Patent: July 18, 1989
    Assignee: National Starch and Chemical Corporation
    Inventors: Robert D. Rossi, Steven P. Fenelli
  • Patent number: 4845304
    Abstract: A process for producing a fluorobenzaldehyde of the formula: ##STR1## wherein X is a chlorine atom, a bromine atom or an iodine atom, n is an integer of from 1 to 5, and m is an integer of from 1 to 5, provided n.gtoreq.m, which comprises reacting a halogenated benzaldehyde of the formula: ##STR2## wherein X and n are as defined above, with a metal fluoride in the presence of a catalyst, wherein at least one member selected from the group consisting of quaternary phosphonium salts and quaternary ammonium salts is used as the catalyst.
    Type: Grant
    Filed: May 4, 1988
    Date of Patent: July 4, 1989
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yasuo Yoshida, Yoshikazu Kimura
  • Patent number: 4845305
    Abstract: This invention presents a method for the preparation of isophthalaldehyde in an all-aqueous solution using m-xylenediamine, hexamethylenetetramine, and HCl as the only reactants. Such a process permits the preparation of high yield of a high purity product.
    Type: Grant
    Filed: July 7, 1988
    Date of Patent: July 4, 1989
    Assignee: National Starch and Chemical Corporation
    Inventor: Eric A. Meier
  • Patent number: 4820858
    Abstract: The invention relates to a process for the preparation of 2-(hydroxyalkyl)acrylic compounds having the formula ##STR1## wherein X represents a --CN group, a --COOR.sub.3 group, a --COR.sub.4 group or a --CONR.sub.4 R.sub.5 group wherein R.sub.3 is an alkyl group containing 1-4 C atoms and R.sub.4 and R.sub.5 independently represent an H atom or R.sub.3, andwherein R.sub.1 and R.sub.2 independently represent an H atom or an alkyl group with 1-4 C atoms or an (hetero) aryl group, or R.sub.1 and R.sub.2 together represent a cyclic compound with 5-12 C atomsby contacting an acrylic compound H.sub.2 C.dbd.CH--X with a carbonyl compound of the formula ##STR2## wherein X, R.sub.1 and R.sub.2 denote the same as in the above, this being effected in the liquid phase in the presence of a tertiary amine, characterized in that the reaction is carried out at a pressure in excess of 500 bar in excess of 500 bar, advantageously 1,500-18,000 bar.
    Type: Grant
    Filed: March 18, 1988
    Date of Patent: April 11, 1989
    Assignee: Stamicarbon B.V.
    Inventors: Neil S. Isaacs, Jonathan Hill
  • Patent number: 4778928
    Abstract: The preparation of 4,4'-stilbenedialdehydes by reduction of 4,4'-stilbenedinitriles with an aluminium hydride.
    Type: Grant
    Filed: December 10, 1986
    Date of Patent: October 18, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Dieter Reinehr
  • Patent number: 4766249
    Abstract: Alpha, beta-unsaturated carbonyl compounds are hydrolyzed under alkaline conditions in the presence of water to produce additional carbonyl-containing compounds. High yields are obtained when the alkaline catalyst contains hydroxide ion and the pH is maintained in the range of about 11 to about 13.
    Type: Grant
    Filed: December 24, 1986
    Date of Patent: August 23, 1988
    Assignee: Mallinckrodt, Inc.
    Inventors: Keith T. Buck, Anthony J. Boeing, Joseph E. Dolfini, Jerome Glinka
  • Patent number: 4766250
    Abstract: There is disclosed a process for the racemization of amino acids and derivatives thereof. The racemization process of the present invention uses an aromatic aldehyde-containing polymer made from the reaction of a hydroxyaromatic aldehyde with a chloromethylated vinylbenzene polymer under reaction conditions to form an aromatic aldehyde-containing polymer wherein the aldehydic moiety is linked to the polymer through an ether linkage. There is also disclosed a process for the production of the racemization catalyst. Another embodiment of the invention comprises a process for the promotion of the racemization reaction wherein a tertiary amine-containing resin is used as a promoting agent.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: August 23, 1988
    Assignee: Stauffer Chemical Co.
    Inventor: Stanley B. Mirviss
  • Patent number: 4749815
    Abstract: A process for the manufacture of p-tert-butyl-.alpha.-methylhydrocinnamaldehyde which comprises the catalytic rearrangement of p-tert-butylbenzyl propenyl ether is provided.
    Type: Grant
    Filed: February 3, 1987
    Date of Patent: June 7, 1988
    Assignee: Givaudan Corporation
    Inventor: Peter Gygax
  • Patent number: 4740639
    Abstract: The invention relates to a process for the preparation of 2,4-disubstituted-1,5-pentanediols from formaldehyde and at least one simple aldehyde of the formula RCH.sub.2 CHO. More particularly the invention relates to a reaction to produce a 2,4-disubstituted glutaraldehyde wherein the reactant mole ratio of aldehyde/formaldehyde is between 1 and 8. The reaction is carried out in the presence of a secondary amine or secondary amine salt catalyst and leads to higher yields of the 2,4-disubstituted glutaraldehyde. The invention also relates to the production of 2,4-disubstituted-1,5-pentanediols by hydrogenation of the 2,4-disubstituted glutaraldehydes.
    Type: Grant
    Filed: June 12, 1987
    Date of Patent: April 26, 1988
    Assignee: Eastman Kodak Company
    Inventor: William A. Beavers
  • Patent number: 4727197
    Abstract: Described is a process for preparing natural benzaldehyde and acetaldehyde and compositions of matter containing natural benzaldehyde and acetaldehyde as well as products produced thereby and organoleptic utilities thereof, which process comprises the step of contacting with base naturally occurring cinnamaldehyde or a natural product rich in cinnamaldehyde such as Ceylon oil of cinnamon, Ceylon cinnamon bark, Saigon cinnamon bark, cassia oil, Ceylon cinnamon quills, cinnamon leaf oil, oil of cinnamon Madagascar or the like according to the reaction: ##STR1## the reaction taking place in aqueous media and in the presence of a food grade or natural nonionic emulsifier, preferably a nonionic sorbitan derivative emulsifying agent and in the absence of any other reagents.
    Type: Grant
    Filed: February 6, 1987
    Date of Patent: February 23, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Arthur L. Liberman
  • Patent number: 4727058
    Abstract: Described is a process for preparing natural benzaldehyde and acetaldehyde and compositions of matter containing natural benzaldehyde and acetaldehyde as well as products produced thereby and organoleptic utilities thereof, which process comprises the step of contacting with base naturally occurring cinnamaldehyde or a natural product rich in cinnamaldehyde such as Ceylon oil of cinnamon, Ceylon cinnamon bark, Saigon cinnamon bark, cassia oil, Ceylon cinnamon quills, cinnamon leaf oil, oil of cinnamon Madagascar or the like according to the reaction: ##STR1## the reaction taking place in aqueous media and in the presence of a food grade or natural nonionic emulsifier, preferably a nonionic sorbitan derivative emulsifying agent and in the absence of any other reagents.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: February 23, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Arthur L. Liberman
  • Patent number: 4723042
    Abstract: Alpha,beta-substituted acroleins of the general formula I ##STR1## where A and B are identical or different and are each C.sub.1 -C.sub.4 -alkyl, naphthyl, biphenyl or phenyl which may be monosubstituted or polysubstituted by halogen, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, phenoxy or phenylsulfonyl, are prepared by a process in which a compound of the general formula III ##STR2## where A has the above meanings and R.sup.1 and R.sup.2 are identical or different and are each C.sub.1 -C.sub.4 -alkyl or together possess the carbon atoms required to complete a ring, is reacted with a phosphorus compound of the general formula IV or V ##STR3## where B the meanings stated above, R.sup.1 and R.sup.2 are as defined above and X.sup..crclbar. is a halide ion, in the presence of a base. The alpha,beta-substituted acroleins can be further processed to give hydroxymethyloxiranes.
    Type: Grant
    Filed: January 22, 1987
    Date of Patent: February 2, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Stefan Karbach, Hans-Gert Recker, Marco Thyes