Aldehyde Or Ketone Reactant Patents (Class 568/312)
  • Patent number: 5166450
    Abstract: This invention relates to an improved process for the production of hydroxyketones, especially dihydroxyacetone, by the condensation of one or more aldehydes in the presence of a catalyst and the use of specific process train. The product of this process is a relatively pure and any waste products from the reaction are environmentally friendly because none of the chemical components are discharged into the waste streams.
    Type: Grant
    Filed: October 4, 1991
    Date of Patent: November 24, 1992
    Assignee: BP Chemicals Limited
    Inventors: Carl A. Avison, Ian D. Dobson, Benjamin P. Gracey, Barry Hudson, Thakor Kikabhai
  • Patent number: 5162586
    Abstract: The conjugate addition of hydrocarbon equivalents to alpha,beta-unsaturated carbonyl compounds using a series of novel catalysts is described. The catalysts comprise copper(I) complexes with ligand systems comprising either tropocoronand macrocycles or N,N'-dialkylsubstituted aminotroponeimines.
    Type: Grant
    Filed: May 9, 1989
    Date of Patent: November 10, 1992
    Assignee: Massachusetts Institute of Technology
    Inventors: Gilberto M. Villacorta, Kwang-Hyun Ahn, Stephen J. Lippard
  • 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: 5136081
    Abstract: The invention provides a process for the preparation of fungicidally active cyclopentene derivatives of the general formula ##STR1## cyclopentane derivatives of the general formula ##STR2## and cyclohexane derivatives of the general formula ##STR3## in which n, R, R.sup.1, R.sup.2, R.sup.5, X and Y are as herein defined. Compounds of formula II and III are also provided which are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: August 4, 1992
    Assignee: Shell Internationale Research Maatschappij B.V.
    Inventor: Paul H. Briner
  • 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: 5087761
    Abstract: This invention relates to a process for condensing aldehydes to alpha-hydroxyketones in a liquid system containing an aldehyde and an active condensation catalyst formed by the abstraction of HX from a thiazolium salt in which X is the anion. The reaction is carried out in the absence of a base (other than the active catalyst) and the anion X. The catalyst is rendered free of the undesirable base and the anion X because these are the cause of premature deactivation of the catalyst.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: February 11, 1992
    Assignee: BP Chemicals Limited
    Inventor: Thakor Kikabhai
  • 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: 5023382
    Abstract: 2,3-disubstituted-2-cyclopenenones (such as cisjasmone) are prepared by (a) reacting an alkl 2-chloro-2,3-disubstituted-3-butenoate with a lithiomercaptan compound, (b) subjecting that product to reductive dehydrosulfurization. Methods of preparing the reactants are also disclosed.
    Type: Grant
    Filed: January 24, 1990
    Date of Patent: June 11, 1991
    Assignee: Petrolite Corporation
    Inventor: Jacob Mathew
  • Patent number: 4973756
    Abstract: An alpha-hydroxyl-alpha,alpha-di(inert-substituted)-gamma',delta'-yne ketone can be prepared by a procedure comprising contacting an acetylenic Grignard reagent with an alpha-hydroxyl-alpha,alpha-di(inert substituted)-alpha',beta'-ene ketone, and the alpha-hydroxyl-alpha,alpha-di(inert-substituted)-alpha',beta'-ene ketone can be prepared by a procedure comprising steps of contacting, first, an alkoxy allene with a lithium donating organic agent, second, product of the first step with a di(inert-substituted)ketone, and third, product of the second step with an acidic substance.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: November 27, 1990
    Assignee: Marion Laboratories, Inc.
    Inventors: Hans Wynberg, Wolter T. Hoeve, Gerrit A. Barf, Johannes N. Koek, David R. Borcherding
  • Patent number: 4952708
    Abstract: An improved method for making biaryl compounds is disclosed, in which an aromatic acid halide having at least one strong electron-withdrawing group attached to or within the aromatic ring is reacted with at least one polysilane in the presence of an effective amount of a transition metal catalyst.
    Type: Grant
    Filed: April 3, 1989
    Date of Patent: August 28, 1990
    Assignee: General Electric Company
    Inventors: Jonathan D. Rich, Terry E. Krafft, Philip J. McDermott, Tony C. Chang
  • Patent number: 4912262
    Abstract: According to the present invention there is provided process for preparing a compound of formula (I): ##STR1## or a salt, acylate or sulphonate derivative thereof; wherein R.sup.1 is an optionally substituted aryl group, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are selected from hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkanoyl or --CO.sub.2 R.sup.a wherein R.sup.a is C.sub.1-4 alkyl or R.sup.2 and R.sup.3 or R.sup.4 and R.sup.5 together with the carbon atom to which they are attached form a C.sub.3-6 cycloalkyl ring, provided that at least R.sub.2 and R.sup.3 or R.sup.4 and R.sup.5 are not both hydrogen and that not more than two of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are C.sub.1-4 alkanoyl or --CO.sub.2 R.sup.a ; which process comprises reacting a compound of formula (II): ##STR2## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in relation to formula (I) with a compound of formula (III):R.sup.1 COCN (III)wherein R.sup.
    Type: Grant
    Filed: March 7, 1988
    Date of Patent: March 27, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventor: Glynn Mitchell
  • 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: 4740624
    Abstract: Ketones of the formula II ##STR1## with Ar, R.sup.1 and R.sup.2 as indicated below, can be hydroxylated, readily and in high yields, in the .alpha.-position using tetrahalogenomethanes and alkali metal hydroxides under phase-transfer conditions.
    Type: Grant
    Filed: April 7, 1986
    Date of Patent: April 26, 1988
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Manfred Kohler, Michael Romer, Claus P. Herz
  • Patent number: 4721815
    Abstract: There is disclosed a process for the preparation of a benzophenone, which process comprises contacting a feed comprising a 3-cyclohexene carboxylic acid in the vapor phase and under suitable conditions with a ketonic decarboxylative coupling catalyst to convert said carboxylic acid into a bis (3-cyclohexene) ketone and contacting said bis (3-cyclohexene) ketone with a dehydrogenation catalyst to dehydrogenate said bis (3-cyclohexene) ketone to provide said benzophenone. Suitably, the coupling catalyst comprises an oxide of manganese. A Group VIII metal-containing catalyst is a typical dehydrogenation catalyst.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: January 26, 1988
    Assignee: Amoco Corporation
    Inventors: Gregory P. Hussmann, Carl A. Udovich
  • Patent number: 4670577
    Abstract: A novel process for the preparation of pent-4-enoic acids of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, cyano and alkoxycarbonyl of 2 to 5 carbon atoms and Y is selected from the group consisting of hydrogen, cyano, alkoxycarbonyl 2 to 5 carbon atoms, acyl of an organic carboxylic acid of 2 to 7 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms and arylsulfonyl of 6 to 7 carbon atoms with the proviso that X and Y are not both hydrogen comprising reacting a compound of the formula ##STR2## wherein R is selected from the group consisting of acyloxy of an organic carboxylic acid of 1 to 7 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms and arylsulfonyl of 6 to 7 carbon atoms with an anion derivative of a compound of the formula ##STR3## wherein X.sub.1 and Y.sub.
    Type: Grant
    Filed: February 24, 1984
    Date of Patent: June 2, 1987
    Assignee: Roussel Uclaf
    Inventors: Marc Julia, Therese Cuvigny
  • Patent number: 4577046
    Abstract: Deamination of aromatic primary amines by diazotization and hydrogen replacement of the diazo group is accelerated in the presence of hydrogen peroxide. Yields of at least about 85% are typical, with reaction times of usually about one hour or less.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: March 18, 1986
    Assignee: University of New Mexico
    Inventors: Mark D. Hylarides, Fred A. Mettler, Jr.
  • Patent number: 4570021
    Abstract: Disclosed is a method for the preparation of ketones by a catalytic vapor phase reaction of using reactants such as ketones with carboxylic acids and/or carboxylic acid precursors. An example of such a reaction is that of acetone with pivalic acid over a ceria-alumina catalyst at a temperature of nearly 470.degree. C. to produce pinacolone.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: February 11, 1986
    Assignee: SDS Biotech Corporation
    Inventors: Richard L. Cryberg, Russell M. Bimber
  • Patent number: 4568768
    Abstract: A method for producing m-hydroxy-acetophenone which comprises allowing m-(2-hydroxy-2-propyl)cumene hydroperoxide to react at 30.degree. to 100.degree. C. in the presence of an aqueous solution containing 0.001 to 1 mole of iron salt per mole of said compound, 0.01 to 4 moles of copper salt per mole of said iron salt, and mineral acid to give m-(2-hydroxy-2-propyl)acetophenone, then allowing the resulting compound to react at 30.degree. to 95.degree. C. in the presence of 1 to 20 moles of 5 to 90% by weight aqueous hydrogen peroxide solution per mole of said compound and acid catalyst to form m-(2-hydroperoxy-2-propyl)acetophenone, and further subjecting the product formed to acid decomposition. m-Hydroxyacetophenone is an important intermediate in the fields of pharmaceuticals, agricultural chemicals, dyestuffs and the like.
    Type: Grant
    Filed: December 13, 1984
    Date of Patent: February 4, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Nakamura, Seiichi Kai, Nobuharu Kono
  • Patent number: 4567005
    Abstract: Carbon acids are allylated by contacting with an allyl carbonate in the presence of an iron, cobalt, nickel, ruthenium, rhodium, osmium, iridium or platinum catalyst.
    Type: Grant
    Filed: April 22, 1983
    Date of Patent: January 28, 1986
    Assignee: The Dow Chemical Company
    Inventor: Edmund P. Woo
  • Patent number: 4546184
    Abstract: The invention relates to a novel fluorinated pre-polymer and novel process steps in producing the same. The pre-polymers are quinoxaline materials derived by reaction of diketone linkage containing perfluoro-compounds with an aromatic diamine. The diketone is produced by oxidatively dechlorinating a polychloroketone which may be a monoketone or a bis-ketone. The polychloroketone is produced by reacting a keto-ylid with a chlorinating agent, e.g., chlorine. The keto-ylid is produced by reacting a phosphorane with an acid halide of a polyoxy-perfluoroalkylene oxide wherein the perfluoro-oxyalkylene group contains two or three carbon atoms, and there are present from two to twenty perfluoro-oxyalkylene units in the oligomer. The quinoxalines, the polychloroketones and the diketones hereof are novel products. Cross-linking may be effected with a free radical generator.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: October 8, 1985
    Assignee: SCM Corporation
    Inventor: Keith B. Baucom
  • Patent number: 4542233
    Abstract: Improvement in the process for preparing biaryl compounds via coupling of an arylamine with an arene in the presence of a nitrite, an acid and copper metal or a derivative thereof; the improvement is consisting in adding to the reaction mixture a trialkylorthoformate. The process may be used for preparing drugs such as Flurbiprofen and Xenbucin or intermediate compounds particularly useful for preparing Flurbiprofen, Flufenisal, Chlordimorin, Xenbucin, Xenysalate, Xenyhexenic acid and the like.
    Type: Grant
    Filed: July 20, 1983
    Date of Patent: September 17, 1985
    Assignee: Biaschim S.p.A.
    Inventors: Oreste Piccolo, Aldo Belli, Giovanni Villa, Enrico Zen, Attilio Citterio
  • Patent number: 4536347
    Abstract: Ruthenium-on-charcoal and ruthenium-on-carbon black catalysts, containing from 0.1 to 5% by weight of iron, for the preparation of olefinically unsaturated alcohols by selective hydrogenation of the corresponding .alpha., .beta.-unsaturated carbonyl compounds in the liquid phase are prepared by modifying the catalyst with iron only after it has been impregnated with the ruthenium compound, and reducing the catalyst with hydrogen at from 400.degree. to 600.degree. C., with thorough mixing.The catalysts according to the invention are particularly useful for improving the industrially difficult hydrogenation of citral to give the soughtafter fragrances geraniol and nerol.
    Type: Grant
    Filed: March 19, 1984
    Date of Patent: August 20, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Horner, Matthias Irgang
  • Patent number: 4510321
    Abstract: Processes for the autoxidative cleavage of selected ketones such as C.sub.4 -C.sub.10 cycloalkanones having at least one hydrogen or at least one R group on a carbon alpha to the carbonyl carbon or aryl alkyl ketones having the formula III ##STR1## comprising contacting a liquid phase comprising said ketone with elemental oxygen gas, preferably air, in the presence of a pulverized alkali metal hydroxide at a temperature of no more than 50.degree. C. for a time sufficient to produce an oxidized product are disclosed. Preferred cycloalkanones, 2-alkyl- and 2-arylcyclohexanone are autoxidized in pulverized sodium hydroxide/dimethoxyethane to produce 6-alkyl- or 6-aryl-6-oxohexanoic acids, respectively.
    Type: Grant
    Filed: January 31, 1983
    Date of Patent: April 9, 1985
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Edward H. Manahan
  • Patent number: 4497827
    Abstract: Novel compounds of this invention are tetrazole, acylhydroxylamine, hydroxymethylketone and amide derivatives of unsaturated fatty acids which are selective inhibitors of the enzymes lipoxygenase and cyclooxygenase involved in the production of pain, inflammation, bronchoconstriction and allergic reactions. These compounds are beneficial in the treatment of a number of inflammatory and/or painful conditions and allergic reactions.
    Type: Grant
    Filed: August 30, 1982
    Date of Patent: February 5, 1985
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Peter H. Nelson
  • Patent number: 4487969
    Abstract: A process for the production of m-fluoroacetophenone comprises reacting m-aminoacetophenone with a diazotization agent in the presence of hydrogen fluoride. The diazonium fluoride compound produced is decomposed by heating to produce highly pure m-fluoroacetophenone in good yields.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: December 11, 1984
    Assignee: Olin Corporation
    Inventor: Max M. Boudakian
  • Patent number: 4476324
    Abstract: Heat treated anionic clay mineral is an improved catalyst for the conversion of acetone to mesityl oxide and isophorone as well as for the aldol condensation of other carbonyl-containing compounds.
    Type: Grant
    Filed: June 2, 1982
    Date of Patent: October 9, 1984
    Assignee: Union Carbide Corporation
    Inventor: Walter T. Reichle
  • Patent number: 4453018
    Abstract: An alkylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with an alkyl sulfite of the formula (RO).sub.2 SO in which R is a one to four carbon alkyl group, the reaction occurring in one step and without the intermediate preparation of a phenolate.
    Type: Grant
    Filed: April 1, 1982
    Date of Patent: June 5, 1984
    Assignee: International Telephone and Telegraph Corporation
    Inventor: Randall B. Nelson
  • Patent number: 4453017
    Abstract: A methylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with trimethyl phosphate, the reaction occurring in one step and without the intermediate preparation of a phenolate.
    Type: Grant
    Filed: April 1, 1982
    Date of Patent: June 5, 1984
    Assignee: International Telephone and Telegraph Corporation
    Inventor: Randall B. Nelson
  • Patent number: 4449001
    Abstract: Oxy- and thio-aryl-phenylated aromatic biscyclopentadienones are prepared from aromatic bis-benzils and benzylketones.
    Type: Grant
    Filed: March 8, 1983
    Date of Patent: May 15, 1984
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Bruce A. Reinhardt, Fred E. Arnold
  • Patent number: 4422870
    Abstract: 2-Aryl-1, 3-cyclohexanedione enol ester compounds exhibit outstanding miticidal,mite ovicidal and herbicidal activity.
    Type: Grant
    Filed: March 28, 1977
    Date of Patent: December 27, 1983
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4402862
    Abstract: The invention relates to the stabilization against water uptake of hygroscopic salts useful as catalysts by formation of anhydrous adducts with particulate support materials in order to facilitate manipulation and storage. The adducts comprise a particulate support material and a hygroscopic salt of a species of formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 N, R.sup.1 R.sup.2 R.sup.3 R.sup.4 P, R.sup.1 R.sup.2 R.sup.3 R.sup.4 As, wherein R.sup.1 R.sup.4 which may be identical or different represent hydrogen or alkyl or aryl groups, or of Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, Cu.
    Type: Grant
    Filed: May 20, 1982
    Date of Patent: September 6, 1983
    Assignee: National Research Development Corporation
    Inventor: James H. Clark
  • Patent number: 4391982
    Abstract: The present invention provides compounds having the structure: ##STR1## wherein R.sup.1 represents alkoxy or aralkoxy, R.sup.2 represents hydrogen, alkoxy, aralkoxy, alkyl, aralkyl, or R.sup.1 and R.sup.2 taken together represent the group --O--CH.sub.2 --O--, R.sup.3 represents hydrogen, alkyl, aralkyl, acyl or a protecting group, Y represents Cl, Br, I or a leaving group; and X represents Cl, Br or I.The present invention also provides a process for preparation of compounds VI in a single step wherein X and Y are the same and represent Cl, Br, ,or I, and R.sup.3 is as previously defined except that in this instance, it does not represent a protecting group.According to another aspect of the present invention there are provided compounds VII-a and VII-b having the structure: ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as previously defined, j is an integer having a value of 0 or 1, Z.sup.1 represents a non-reacting electron withdrawing group, and Z.sup.
    Type: Grant
    Filed: March 25, 1981
    Date of Patent: July 5, 1983
    Assignee: The University of Rochester
    Inventors: Andrew S. Kende, Dennis P. Curran, Margaret L. King, Neil A. Feldstein
  • Patent number: 4385070
    Abstract: Compounds of formula I wherein R.sup.1 and R.sup.2 are each selected from halomethyl and halo and R is nitro, cyano, lower alkoxycarbonyl, lower alkylcarbonyl, or di- or trifluoromethyl, and n has a value of zero to four, and compositions comprising them are useful as insecticides in agriculture, horticulture and other outlets. They may optionally be combined with other pesticides and/or synergists. The compounds may be prepared by conventional esterification processes from the corresponding acids and appropriately substituted benzyl alcohols or halides, some of which are novel.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: May 24, 1983
    Assignee: Imperial Chemical Industries Limited
    Inventors: Philip D. Bentley, Nazim Punja
  • Patent number: 4358460
    Abstract: There is disclosed substituted alkenones of Formula I ##STR1## wherein R.sup.1 is alkyl or acylamino each having 1 to 4 carbon atoms, hydrogen, or halogen,R.sup.2 and R.sup.3 individually are hydrogen, methyl or ethyl,R.sup.4 is hydrogen or dimethoxyphenyl, andn is 1 or 2,or physiologically acceptable acid addition salts thereof. Intermediates are also disclosed, along with methods of preparation of both the intermediates and the end products.The end products are useful as .beta. adrenolytic and anti-hypertensive agents. They are useful in the treatment of angina pectoris, hypertension, and arrhythmia.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: November 9, 1982
    Assignee: Beiersdorf Aktiengesellschaft
    Inventor: Erich Cohnen
  • Patent number: 4347192
    Abstract: Derivatives of .alpha.,.beta.-unsaturated ketones having anticonvulsant activity and methods of their preparation from heterocyclic phosphonium salts and acyclic phosphoranes are disclosed.
    Type: Grant
    Filed: July 24, 1980
    Date of Patent: August 31, 1982
    Assignee: G. D. Searle & Co.
    Inventor: Richard A. Mueller
  • Patent number: 4310699
    Abstract: Bis (phenylglyoxyloyl) benzenes are manufactured by a method comprising the reaction of terephthalic or isophthalic aldehyde first with a low proportion of an alkali metal cyanide in a solvent, and then with benzaldehyde; the resultant product is oxidized to the desired bis (phenylglyoxyloyl) benzene.
    Type: Grant
    Filed: May 23, 1980
    Date of Patent: January 12, 1982
    Assignee: Institut Francais du Petrole
    Inventors: Guy Rabilloud, Bernard Sillion
  • Patent number: 4288613
    Abstract: A method of synthesis of cyclopentanones comprising cyclizing a 4-pentenal, preferably under an ethylene atmosphere, in the presence of a catalytically effective amount of a cyclizing, rhodium(I) para-substituted triarylphosphine catalyst.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: September 8, 1981
    Assignee: Iowa State University Research Foundation, Inc.
    Inventor: Richard C. Larock
  • Patent number: 4271319
    Abstract: The present invention relates to a novel organic compound, phenyl beta-chloro-alpha-hydroxy-beta-(3-trifluoromethylphenyl)ethyl ketone. This compound may be produced by:(a) condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone,(b) epoxidation of the substituted chalcone to produce the corresponding epoxide, and(c) converting the epoxide to a chlorohydrin, phenyl beta-chloro-alpha-hydroxy-beta-(3-trifluoromethylphenyl)ethyl ketone.
    Type: Grant
    Filed: May 14, 1979
    Date of Patent: June 2, 1981
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4252739
    Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yields. The process involves reacting an alkylating agent and an activated methylene compound in the presence of an onium compound, an alkali metal compound and water, which while only necessary in trace amounts can be present in substantial quantities.
    Type: Grant
    Filed: August 20, 1979
    Date of Patent: February 24, 1981
    Assignee: Emery Industries, Inc.
    Inventors: Richard G. Fayter, Jr., John F. White, Eugene G. Harris
  • Patent number: 4241206
    Abstract: The invention is a generalized hydroacylation reaction. The reaction involves the activation of a selected aldehyde by converting by iminization to an aldimine or an aminal. The imine group replaces the carbonyl group. The imine C-H bond is then susceptible to attack by a chosen olefin, and hydrolysis to yield the ketone. One moiety of the ketone derives from the aldehyde and the other from the olefin added later. Therefore, the ketone may be symmetrical or unsymmetrical. Both aromatic and aliphatic aldehydes may be activated according to this process.
    Type: Grant
    Filed: October 27, 1978
    Date of Patent: December 23, 1980
    Assignee: Bell Telephone Laboratories, Incorporated
    Inventor: John W. Suggs
  • Patent number: 4221713
    Abstract: Cyclisation substrates are disclosed of the formula: ##STR1## wherein: (a) R.sub.1 is H or alkyl of one to four carbon atoms;(b) R.sub.2 is H or alkyl of one to four carbon atoms, with the proviso that R.sub.1 is H when R.sub.2 is alkyl, and with the proviso that R.sub.2 is H when R.sub.1 is alkyl;(c) R.sub.3 is a suitable leaving group selected from the group consisting of hydroxy, alkoxy of one to four carbons, alkoxyalkoxy of two to four carbons, acyloxy of one to about seven carbon atoms, and trialkylsilyloxy of less than fifteen carbons;(d) R.sub.4 is methyl; and(e) R.sub.5(1) and R.sub.
    Type: Grant
    Filed: October 23, 1978
    Date of Patent: September 9, 1980
    Assignee: Akzona Incorporated
    Inventors: Filippus J. Zeelen, Marinus B. Groen