Halogen Containing Reactant (e.g., Dehydrohalogenation, Etc.) Patents (Class 568/323)
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Publication number: 20040059160Abstract: A process is provided for the production of 2,7-dibromofluorenone. According to the process, a 2,7-dibromofluorene-contianing raw material is oxidized with molecular oxygen in the presence of a phase transfer catalyst such as a quaternary ammonium salt in a heterogeneous, mixed solvent of an aqueous solution of a caustic alkali and a water-insoluble organic solvent. Crude crystals of 2,7-dibromofluorenone, which have been obtained by the oxidization, can be purified by recrystallization to recover 2,7-dibromofluorenone as crystals having a purity of at least 99 wt. %.Type: ApplicationFiled: September 23, 2003Publication date: March 25, 2004Applicant: JFE CHEMICAL CORPORATIONInventors: Youko Sugio, Naoyuki Kitamura, Hiroaki Mori, Tetsuo Hachiya
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Publication number: 20040024257Abstract: The invention concerns a method for sulphonylating a hydroxylated organic compound. The invention concerns in particular aliphatic hydroxylated compounds and more particularly those which comprise on their aliphatic chain, an electroattractive group. The method for sulphonylating a hydroxylated organic compound is characterised in that it consists in reacting said compound, with a sulphonylating agent, in the presence of a sufficient amount of a Lewis acid.Type: ApplicationFiled: August 11, 2003Publication date: February 5, 2004Inventors: Johann Vastra, Laurent Saint-Jalmes
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Patent number: 6667422Abstract: A process for preparing an &agr;-haloketone of the formula (1) where R1 is an optionally heteroatom-containing and optionally substituted hydrocarbon radical, R2 is a hydrogen, alkyl, aralkyl or aryl radical, and X is a halogen radical, by reacting a carboxylic acid derivative of the general formula (2) where L is a leaving group, with a mono- or dienolate of a silyl ester of the formula (3) where R3 and R4 are identical or different alkyl, aryl, alkenyl or aralkyl radicals; and hydrolyzing the reaction product immediately afterwards by adding acid and decarboxylating to (1). The product &agr;-haloketone may be reduced to the corresponding &agr;-haloalcohol.Type: GrantFiled: September 3, 2002Date of Patent: December 23, 2003Assignee: Consortium fuer Elektrochemische Industrie GmbHInventors: Dieter Heldmann, Juergen Stohrer
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Patent number: 6548710Abstract: The present invention relates to a process for preparing 1-indanones of formula I: and isomers thereof, wherein R1, R2, R3, R4, R5, and R6 independently represent H or a C1-C20 hydrocarbon group or R1 and R2 or R2 and R3 or R3 and R4 and/or R5 and R6 together with the carbon atoms to which they are attached form a saturated or unsaturated 5- or 6-membered ring, said hydrocarbon group and/or said ring optionally containing one or more hetero atoms, said ring optionally being substituted with a C1-C4 hydrocarbon group, said process comprising reacting a compound of formula II: wherein R1, R2, R3, R4, R5, and R6 have the same meaning as defined above, with a chlorinating agent, followed by reaction with a Friedel-Crafts catalyst. The invention further relates to the preparation of the corresponding indenes.Type: GrantFiled: October 31, 2001Date of Patent: April 15, 2003Assignee: Akzo Nobel N.V.Inventor: Richard Herman Woudenberg
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Patent number: 6525226Abstract: A process for Friedel-Crafts type liquid-phase alkylation or acylation of an aromatic compound using a hydrotalcite-type basic anionic clay catalyst represented by a formula: [(M2+)1−x(M3+)x(OH)2]x+[Ay−]x/y q H2O where M2+ is a divalent cation selected from Mg2+, Zn2+, Ni2+, Co2+, Mn2+, Cu2+ or a mixture thereof, M3+ is a trivalent cation selected from Ga3+, In3+ Al3+, Fe3+ Cr3+ or a mixture thereof; x is a mole fraction of trivalent cations in the range of about 0.05 to about 0.5; O is oxygen; H is hydrogen; Ay− is an anion; y minus is an anionic negative charge having a value of 1 minus or 2 minus; and q is a number of water molecules, as the water of hydration; and involving following steps: i.Type: GrantFiled: July 1, 2002Date of Patent: February 25, 2003Assignee: Council of Scientific and Industrial ResearchInventors: Vasant Ram chandra Choudhary, Suman Kumar Jana
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Publication number: 20030036668Abstract: Novel techniques are disclosed for the direct fluoridation of organic compounds by treatment with fluorine gas in a reaction mixture comprising hydrofluoric acid and at least one of water and formic acid. The techniques are particularly applicable to aromatic organic compounds and beta-dicarbonyl compounds. Increased efficiency of reaction is observed, together with improvements in yield and purity of product, with especially beneficial effects being apparent at low temperatures.Type: ApplicationFiled: June 3, 2002Publication date: February 20, 2003Inventors: Roy Dennis Bowden, John Steward Moilliet
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Patent number: 6476253Abstract: The present invention relates to a process for preparing monoacetylated hydroquinone compounds of the formula I, to the novel final products of the process and to a process for preparing the precursors.Type: GrantFiled: October 3, 2000Date of Patent: November 5, 2002Assignee: BASF AktiengesellschaftInventors: Karin Schein, Kai-Uwe Baldenius, Wolfgang Siegel, Rainer Stürmer, Detlef Ruff, Hagen Jaedicke
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Patent number: 6437191Abstract: A process for the liquid phase acylation of aromatic compounds by acyl halides to corresponding acylated aromatic compounds, using a reusable solid catalyst comprising indium halide represented by a formula: MxIn1−xAy(a)/s wherein, S is a porous catalyst support selected from clays, zeolites and zeolite-like materials; M is a metallic chemical element(s) selected from the group consisting of Ga (gallium), Fe (iron), Zn (zinc), Ti (titanium) and a mixture of two or more thereof; In is a metallic chemical element, indium; A is a non-metallic chemical element selected from the group consisting of Cl (chlorine), Br (bromine), I (iodine), F (fluorine) and a mixture of two or more thereof; is mole fraction of M in the metallic elements in the range from 0.01 to 0.99; y is the number of A atoms required to satisfy the valence requirement of MxIn1−x; and a is the loading of MxIn1−x A on the support, S, in the range from 0.05 mmol.g−1 to 5.0 mmol.Type: GrantFiled: November 28, 2000Date of Patent: August 20, 2002Assignee: Council of Scientific and Industrial ResearchInventors: Vasant Ramchandra Choudhary, Suman Kumar Jana, Nilesh Sudhir Patil
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Patent number: 6420608Abstract: A process for the preparation of a compound of formula I wherein Y is a group that is inert during preparation of the compound and m is from 0 to 4 is described. The process broadly involves the steps of a) reacting a compound of formula II wherein X is chlorine, bromine or iodine, and Y and m are as defined above, with a vinylether or an enamide in a solvent, a base and a catalytic amount of a palladium compound and a phosphine ligand. The resulting intermediate is then hydrolyzed to the compound of formula I.Type: GrantFiled: December 16, 1999Date of Patent: July 16, 2002Assignee: Bayer AktiengesellschaftInventor: Adriano Indolese
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Patent number: 6417357Abstract: This invention relates to a novel, inventive process for the preparation of biphenyls or aromatic olefins by coupling reactions of the Suzuki coupling and Heck coupling type, using allylpalladium catalysts of the &mgr;-halo(triisopropylphosphine)(&eegr;3-allyl)palladium(II) type.Type: GrantFiled: September 14, 2000Date of Patent: July 9, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Michael Tinkl, Andreas Hafner
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Patent number: 6410796Abstract: Acetophenones which are di- or polysubstituted by fluoroalkyl groups on the aromatic ring are prepared in a particularly advantageous manner from the corresponding fluoroalkylanilines and acetaldoxime by preparing a corresponding diazonium salt mixture from the fluoroalkylaniline, reacting this mixture with acetaldoxime in the presence of at least one copper and/or palladium compound, without adding buffer salts or a reducing agent, carrying out the reaction with acetaldoxime at 5 to 50° C. and in the presence of halide ions and at least one strong acid that is not a hydrohalic acid, and finally heating the mixture to a temperature in the range 70 to 160° C.Type: GrantFiled: December 8, 2000Date of Patent: June 25, 2002Assignee: Bayer AktiengesellschaftInventors: Wulf Kühnle, Thomas Höpfner
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Patent number: 6348631Abstract: The present invention relates to a process for the acylation or sulphonylation of an aromatic compound. More particularly, the invention relates to a process for the acylation or sulphonylation of an activated or deactivated aromatic compound. The invention is applied to the preparation of aromatic ketones or sulphones. The process for the acylation or sulphonylation of an aromatic compound which consists in reacting at least one aromatic compound with an acylating or sulphonylating agent, in the presence of a Friedel-Crafts catalyst is characterized in that the acylation or sulphonylation reaction is carried out in liquid phase under microwave irradiation.Type: GrantFiled: November 22, 1999Date of Patent: February 19, 2002Assignee: Rhodia ChimieInventors: Jean-Roger Desmurs, Jacques Dubac, Andre Laporterie, Christian Laporte, Julien Marquie
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Publication number: 20020016512Abstract: This invention relates to a ligandless process wherein heterogeneous Pd catalysts are used to activate aryl and heteroaryl chlorides for cross coupling aryl and heteroaryl chlorides and boronic acids. The process provides for use with either electron-withdrawing or electron-donating substituents, for cross coupling with boronic acids.Type: ApplicationFiled: July 16, 2001Publication date: February 7, 2002Inventors: Yongkui Sun, Carl LeBlond, John R. Sowa
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Publication number: 20020016511Abstract: A first process for producing an optically active perfluoroalkylcarbinol derivative includes (a) reacting an optically active imine with a compound that is a hemiacetal of a perfluoroalkylaldehyde or a hydrate of a perfluoroalkylaldehyde to obtain a condensate; and (b) hydrolyzing the condensate under an acid condition. A second process for increasing optical purity of an optically active 4,4,4-trifluoro-3-hydroxy-1-aryl-1-butanone derivative includes (a) precipitating a racemic crystal of the derivative, from the derivative; and (b) removing the racemic crystal from the derivative. A third process for increasing optical purity of the butanone derivative includes recrystallizing the derivative. Novel compounds are optically active and inactive 4,4,4-trifluoro-3-hydroxybutanoic aryl ester derivatives.Type: ApplicationFiled: January 29, 2001Publication date: February 7, 2002Inventors: Akihiro Ishii, Masatomi Kanai, Takashi Hayami, Katsuyoshi Shibata, Masaki Matsui, Kazumasa Funabiki, Yokusu Kuriyama, Manabu Yasumoto
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Patent number: 6303812Abstract: Disclosed is a method of isolating the aromatic product formed when a substrate having the general formula is dehalogenated, forming a product mixture of copper salts and aromatic product, where X is the halogen removed from the substrate to form the aromatic product, R′ is COOH, COOR, COR, CN, COH(R)2, or SO3H, each R″ is independently selected from halogen, R, or OR or two vicinal R″ groups form one or more fused aromatic rings, R is alkyl from C1 to C18 or aryl from C6 to C18, and n is 1 to 4. Water in an amount about 1 to about 5 times the amount of the substrate is added to the product mixture, forming an organic phase that contains the aromatic product and an aqueous phase that contains the copper salts. If the density of the organic phase differs from the density of said aqueous phase by less than 0.1 g/cc, a suitable solvent is added to the product mixture in an amount sufficient to increase the differences between the organic and aqueous phases to at least 0.Type: GrantFiled: February 15, 2000Date of Patent: October 16, 2001Assignee: Occidental Chemical CorporationInventors: Michael J. Fifolt, Michael C. Savidakis, Ronald Spohn, Daniel R. Thielen, William S. Derwin, David C. Johnson
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Patent number: 6300522Abstract: A process is provided for the preparation of compounds of Formula (1): wherein X1 and X2 are each independently H, Cl or F, provided that at least one of X1 and X2 is Cl or F; one of R1 and R2 is H and the other is OH; and R5 is an unsubstituted alkyl, preferably a C1-6 alkyl, group.Type: GrantFiled: November 29, 2000Date of Patent: October 9, 2001Assignee: Avecia LimitedInventors: John Crosby, Kevin Douglas Bailey, Michael John Monteith
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Patent number: 6281400Abstract: The present invention relates to a process for preparing a microcomposite comprising a highly fluorinated ion-exchange polymer containing pendant sulfonate functional groups, said polymer existing as aggregated particles entrapped within and dispersed throughout a network of silica. Due to their high surface area and acid functionality, these microcomposites possess wide utility as improved solid acid catalysts, particularly in the substitution of aromatic compounds, in the decomposition of hydroperoxides, and in the isomerization of olefins.Type: GrantFiled: January 14, 2000Date of Patent: August 28, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Qun Sun
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Patent number: 6274770Abstract: There is disclosed a process for the preparation of a compound of general formula (I), wherein Y and Z each independently represent a fluorine atom or a hydroxy group, and a, b, c and d independently represent 0, 1, 2 or 3 provided that the sum of a, b, c, and d is 1, 2, 3 or 4; the process comprising treating a compound of general formula (II), wherein a, b, c, and d are as described above and L1 and L2 each independently represent an active group provided that either Y and L1 are different or Z and L2 are different, with a fluorinating system in the presence of oxygen. A preferred compound of general formula (I) is 4,4′-difluorobenzophenone which may be prepared from 4,4′-dinitrophenylmethane using tetramethylammonium fluoride.Type: GrantFiled: September 13, 1999Date of Patent: August 14, 2001Assignee: Victrex Manufacturing LimitedInventors: James Hanley Clark, David Adams
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Patent number: 6271421Abstract: A process for selectively debrominating polybromoalkyl aryl ketones and polybromoalkyl heteroaryl ketones is disclosed. The process comprises contacting an alpha-polybrominated ketone with an alkali metal sulfite in the presence of a C2-C6 alkylcarboxylic acid to obtain a selectively mono-debrominated product.Type: GrantFiled: November 12, 1999Date of Patent: August 7, 2001Assignee: Merck & Co., Inc.Inventor: Anthony O. King
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Patent number: 6211399Abstract: Disclosed is a method of adding 1 to 4 chlorine or bromine atoms to an aromatic ring of compound that has at least one electron-withdrawing groups on that ring. The aromatic compound is reacted with a chlorinating agent or a brominating agent in the presence of about 0.1 to about 10 mole % of a Lewis acid catalyst at a temperature of ambient to about 100° C. and a pressure of about 10 to about 100 psig.Type: GrantFiled: October 5, 1999Date of Patent: April 3, 2001Assignee: Occidental Chemical CorporationInventors: Michael C. Savidakis, David C. Johnson
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Patent number: 6211413Abstract: There is provided a process for the preparation of compounds of formula I wherein: X is H or F, Y is CF3 or F and R1 is hydrogen or C1-C2alkyl; in which process (1) a compound of formula II, wherein X and Y are as defined for formula I, is reacted with an organic or inorganic nitrite or nitrous acid; (2) the resulting diazonium compound of formula III is reacted with an aldoxime of formula V R1—CH═NOH (V) wherein R1 is as defined for formula I, in presence of CuSO4; and (3) the resulting oxime of formula IV is hydrolyzed with aqueous acid to the compound of formula I.Type: GrantFiled: January 12, 1999Date of Patent: April 3, 2001Assignee: Bayer AktiengesellschaftInventors: Arthur Wegmann, Terry Lee Moore, Linhua Wang
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Patent number: 6194599Abstract: The present invention provides a process for preparing biaryl compounds comprising reacting an arylzinc reagent with an arylchloride in the presence of a nickel catalyst or a palladium catalyst. The present invention specifically provides a process for the preparation of 2-(4′-methylphenyl)benzonitrile comprising reacting a 4-methylphenylzinc reagent with 2-chlorobenzonitrile in the presence of a nickel catalyst or a palladium catalyst.Type: GrantFiled: April 8, 1997Date of Patent: February 27, 2001Assignee: Catalytica, Inc.Inventors: Joseph A. Miller, Robert P. Farrell
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Patent number: 6184418Abstract: A method for acylating an aromatic compound, specifically an activated or deactivated aromatic compound, is disclosed. The method is suitable for preparing aromatic ketones. The preparation of a catalyst and novel bismuth compounds is also disclosed. Said aromatic compound acylation method comprises reacting said aromatic compound with an acylating agent in the presence of a catalyst, and is characterised in that the acylation reaction is performed in the presence of an effective amount of at least one bismuth salt of trifluoromethanesulphonic acid.Type: GrantFiled: January 19, 1999Date of Patent: February 6, 2001Assignee: Rhodia ChimieInventors: Jacques Dubac, Hafida Gaspard, Mireille Labrouillere, André Laporterie, Jean-Roger Desmurs, Christophe Le Roux
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Patent number: 6147049Abstract: The present invention provides compounds of formula I: ##STR1## wherein R.sup.1 is hydrogen or methyl and R.sup.2 is alkyl. These compounds are useful as fixatives in fragrance compositions. Processes of making such compounds are also provided.Type: GrantFiled: December 13, 1999Date of Patent: November 14, 2000Assignee: Givaudan Roure (International) SAInventors: Peter Gygax, Hans-Ulrich Gonzenbach
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Patent number: 6139770Abstract: An oxygen scavenging composition or system is provided comprising an oxygen scavenging material, a photoinitiator, and at least one catalyst effective in catalyzing an oxygen scavenging reaction, wherein the photoinitiator comprises a benzophenone derivative containing at least two benzophenone moieties. A film, a multi-phase composition, a multi-layer composition, a multi-layer film, an article comprising the oxygen scavenging composition, a method for preparing the oxygen scavenging composition, and a method for scavenging oxygen are also provided. Non-extractable benzophenone derivative photoinitiators and methods for preparing same are also provided.Type: GrantFiled: May 16, 1997Date of Patent: October 31, 2000Assignees: Chevron Chemical Company LLC, Cryovac, Inc.Inventors: Kiyoshi Katsumoto, Ta Yen Ching, Joseph L. Goodrich, Drew Ve Speer
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Patent number: 6133409Abstract: This invention is directed to a process for the solid phase synthesis of aldehyde, ketone, oxime, amine, hydroxamic acid and .alpha.,.beta.-unsaturated carboxylic acid and aldehyde compounds and to polymeric hydroxylamine resin compounds useful therefor.Type: GrantFiled: June 24, 1998Date of Patent: October 17, 2000Assignee: Aventis Pharmaceuticals Products Inc.Inventors: Joseph M. Salvino, George C. Morton, Helen J. Mason, Richard F. Labaudiniere
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Patent number: 6127579Abstract: A method of manufacturing the useful substance 1-indanone from easily obtainable materials consists of reacting an indanyl ether represented by the generic formula ##STR1## under basic conditions to give a novel substance which is the indenyl ether derivative represented by the generic formula ##STR2## and hydrolyzing this to give the 1-indanone represented by the generic formula ##STR3##Type: GrantFiled: July 1, 1999Date of Patent: October 3, 2000Assignee: Ichikawa Gosei Chemical Co., Ltd.Inventors: Shigeru Nakano, Noriko Yoneta, Takashi Tate
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Patent number: 6118018Abstract: Disclosed is a method of adding 1 to 4 chlorine or bromine atoms to an aromatic ring of compound that has at least one electron-withdrawing groups on that ring. The aromatic compound is reacted with a chlorinating agent or a brominating agent in the presence of about 0.1 to about 10 mole % of a Lewis acid catalyst and about 0.001 to about 0.1 equivalents of an iodine-containing cocatalyst at a temperature of ambient to about 100.degree. C.Type: GrantFiled: December 6, 1999Date of Patent: September 12, 2000Assignee: Occidental Chemical CorporationInventors: Michael C. Savidakis, Michael J. Fifolt, Daniel R. Thielen, Ronald Spohn, David C. Johnson, William S. Derwin
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Patent number: 6103938Abstract: 4-(Substituted phenyl)-3,4-dihydro-2H-naphthalen-1-ones, which are useful as intermediates in the preparation of antidepressant agents, are conveniently prepared by reacting 1-substituted naphthalenes and an aromatic moiety in the presence of an acid catalyst. 4-(3,4-Dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one, which is useful as an intermediate in the preparation of the antidepressant sertraline, is conveniently prepared by reacting 1-naphthyl acetate and o-dichlorobenzene in the presence of an acid catalyst.Type: GrantFiled: March 1, 1999Date of Patent: August 15, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Paul A. Odorisio, Stephen D. Pastor, Sai P. Shum
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Patent number: 6096930Abstract: The present invention relates to novel cyclohexane-1-3-dione derivatives of formula (1) useful as herbicides and plant-growth regulants, ##STR1## wherein X is selected from the group consisting of hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, nitro, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 sulfamoyl, and N, N-di(C.sub.1 -C.sub.6 alkyl)sulfamoyl group; (X)n represents the number of X substituents which may be substituted on benzene ring, wherein n is 1, 2 or 3. Also, cyclohexyl moiety, one of the substituents on benzofuran ring, is substituted at C-4, C-5, C-6 or C-7 position on benzene ring; R.sup.1 is selected from the group consisting of hydrogen and C.sub.1 -C.sub.6 alkyl group; R.sup.2 is selected from the group consisting of C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl and C.sub.2 -C.sub.6 alkynyl group; R.sup.3 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.Type: GrantFiled: May 12, 1998Date of Patent: August 1, 2000Assignee: Korea Research Institute of Chemical TechnologyInventors: Eung Kul Ryu, Kyoung Mahn Kim, Jae Nyoung Kim, Jin Seog Kim
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Patent number: 5981803Abstract: An effective and efficient process for the preparation of chloro-benzoylchlorides of formula I, ##STR1## (n is defined in the specification). In this process a a chloro-trichloromethylbenzene of formula II ##STR2## is treated with water acid in the presence of a Lewis at temperatures below 80.degree. C. The compounds obtained according to this process can be used to prepare certain chloro-substituted benzophenones.Type: GrantFiled: January 15, 1999Date of Patent: November 9, 1999Assignee: American Cyanamid CompanyInventors: Laurens Wilhelm van den Akker, Monika Brink
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Patent number: 5969188Abstract: The present invention provides high purity trifluoromethylacetophenones of the general formula:F.sub.3 C--(C.sub.6 H.sub.4)-(C.dbd.O)--CH.sub.3wherein the position of the CF.sub.3 -- group on the aromatic ring may be in the 2-, 3-, or 4- position relative to the acetyl, --(C.dbd.O)--CH.sub.3, group, said trifluoromethylacetophenone being substantially free of other organic or inorganic materials, wherein said trifluoromethylacetophenones are produced by a novel high yield process.Type: GrantFiled: January 5, 1999Date of Patent: October 19, 1999Assignee: NIPA Hardwicke, Inc.Inventor: J. E. Hardwicke, III
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Patent number: 5942636Abstract: The invention relates to a process of preparing a 2-alkyl-2,3-dihydro-1H-benz?e!indene-1-one derivative, preferably 2,3-dihydro-2-methyl-benz?e!indene-1-one, characterized in that a naphthalene derivative is condensed with an active ester of 2-alkyl-2-propenoic acid, preferably with 2-methyl-2-propenoyl chloride. The product which is obtained in high yield and substantially free from its isomer is an intermediate in the preparation of rac-dimethyl bis(2-alkyl-1H-benz?e!indenyl)silandiyl zirconium dichloride complex.Type: GrantFiled: January 22, 1998Date of Patent: August 24, 1999Assignee: Akzo Nobel N.V.Inventors: Richard Herman Woudenberg, Heert Andringa
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Patent number: 5886210Abstract: A method for synthesizing aromatic compounds by selectively dehalogenating aromatic starting materials is provided. Compounds may be prepared which are substituted with fluoro, chloro or bromo. The method may be used to remove halogen atoms from sites at which halogenation is not desired, and to form substantially pure halogenated compounds from mixtures of starting materials. The method uses a copper containing dehalogenation agent and an acid with the dehalogenation being controlled by a substituent such as a carboxylic acid, amide, ester, aldehyde, ketone or cyano on the aromatic ring.Type: GrantFiled: June 16, 1997Date of Patent: March 23, 1999Assignee: Rohm and Haas CompanyInventors: Heather Lynnette Rayle, Randall Wayne Stephens
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Patent number: 5856576Abstract: There are provided aryne intermediates of formula I, useful in the manufacture of herbicidal compounds. ##STR1## Also provided is a method to prepare the formula I intermediates via the palladium catalyzed coupling of an o-halonitrobenzene or o-haloaniline with 3-butyne-1-ol.Type: GrantFiled: January 29, 1998Date of Patent: January 5, 1999Assignee: American Cyanamid CompanyInventors: Philip M. Harrington, Kenneth A. M. Kremer
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Patent number: 5811586Abstract: A process for manufacturing 1-(3-trifluoromethyl)phenyl-propan-2-one intermediate in the synthesis of the anorexic drug fenfluramine consists of reacting the diazonium salt of 3-trifluoromethylaniline with isopropenyl acetate in a polar solvent in the presence of a catalytic amount of a cuprous salt and, optionally, of a base and purifying the crude product through the bisulfite complex or distillation under vacuum.Type: GrantFiled: April 17, 1997Date of Patent: September 22, 1998Assignee: Alfa Chemicals Italiana S.P.A.Inventors: Vincenzo Cannata, Barbara Galbiati, Angelo Spreafico
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Patent number: 5723676Abstract: A process for producing benzophenone compounds is provided. Specifically, a process is provided for producing benzophenone compounds in which a diphenylmethane compound is reacted with manganese dioxide and a strong acid. The process yields the product benzophenone in high purity and good yield.Type: GrantFiled: July 1, 1996Date of Patent: March 3, 1998Assignee: AlliedSignal Inc.Inventors: Lee Alan DeWitt, Heng Su, Chempolil Thomas Mathew
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Patent number: 5679865Abstract: The invention relates to a process for the preparation of polyhydroxybenzophenones by treating benzoic acid or a derivative thereof with a polyhydroxybenzene or a derivative thereof in the presence of a large pore zeolite as a catalyst.Type: GrantFiled: June 21, 1996Date of Patent: October 21, 1997Assignee: Technische Universiteit DelftInventors: Anthonius Johannes Hoefnagel, Herman van Bekkum
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Patent number: 5629454Abstract: Conformationally locked 4',6'-cyclopropane-fused carbocyclic nucleoside analogues. The compounds are prepared by condensing a cyclopropane-fused carbocyclic allylic alcohol with substituted purine or pyrimidine bases. The condensation products are then modified to produce the adenosine, guanosine, cytidine, thymidine and uracil nucleoside analogues. The compounds are therapeutically useful as antimetabolites, or in the preparation of anti-metabolic agents.Type: GrantFiled: September 23, 1994Date of Patent: May 13, 1997Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Victor E. Marquez, Juan B. Rodriguez, Marc C. Nicklaus, Joseph J. Barchi, Jr., Maqbool A. Siddiqui
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Patent number: 5532416Abstract: The present invention relates to novel 4-halo-2-fluoro-5-alkylbenzoyl compounds and their methods of manufacture. These compounds are useful for the preparation of agricultural chemicals and medicines, particularly as intermediates for an active class of aryl-haloalkylpyrazole and aryl alkylsulfonylpyrazole herbicides.Type: GrantFiled: July 20, 1994Date of Patent: July 2, 1996Assignee: Monsanto CompanyInventors: Bruce C. Hamper, Kindrick L. Leschinsky
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Patent number: 5481043Abstract: Certain new phenone derivatives of the formula (I) ##STR1## in which R.sup.1 =CH.sub.3,R.sup.2 =H, Cl, Br, I, methyl, hydroxy, methoxy, propoxy, propoxy or ethoxy;R.sup.3 =H or .beta.-D-glykosyl;R.sup.4 =H, Cl, Br, I, methyl, hydroxy, methoxy, propoxy, iso-propoxy or ethoxy;R.sup.5 =H or hydroxy,and the pharmaceutically acceptable salts, ethers and esters thereof, with the exception of the compounds 4-hydroxyacetophenone, 4-hydroxy-3-methoxy-acetophenone, 4-glucopyranosyloxy-acetophenone, 4-glucopyranosyloxy-3-methoxyacetophenone, 4-galactopyranosyloxy-3-methoxy-acetophenone, 4-glucopyranosyloxy-3,5-dimethoxy-acetophenone and galactopyranosyloxy-3,5-dimethoxy-acetophenone and a method for manufacturing them and pharmaceutical preparations containing them. The invention also concerns pharmaceutical preparations containing at least one compound of the formula (II) ##STR2## in which R.sup.1 denotes H, OH, alkoxy or C.sub.1-8 alkyl;R.sup.2 denotes H or C.sub.1-4 alkoxy;R.sup.3 denotes OH or a .beta.Type: GrantFiled: February 18, 1992Date of Patent: January 2, 1996Assignee: Plantamed Arzneimittel GmbHInventors: Hildebert Wagner, Walter Dorsch, Hermann Stuppner, Sandor Antus
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Patent number: 5476970Abstract: The present invention relates to the production of aryl ketones. Specifically the invention relates to the production of aryl ketones by reaction of aromatic hydrocarbon compounds and benzoyl chloride in the presence of iron (III) chloride. In particular, the invention relates to reaction under conditions of elevated temperature and pressure. Preferred embodiments of the invention specifically relate to the synthesis of benzophenone, methylbenzophenone and dimethylbenzophenone.Type: GrantFiled: February 16, 1984Date of Patent: December 19, 1995Assignee: Velsicol Chemical CorporationInventors: Arlice E. Rains, Terry E. Lea, David I. Templer
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Patent number: 5430015Abstract: A method of acetylating 1,2,3,4,-tetrahydro-1,1,2,4,4,7-hexamethylnapthalene (HMT) to produce 6-acetyl-1,2,3,4-tetrahydro-1,1,2,4,4,7-hexamethlnaphthalene (acetyl-HMT), comprises subjecting a mixture of 1,2,3,4-tetrahydro-1,1,2,4,4,7-hexamethlnaphthalene and or one or more substituted indanes or substituted acetylindanes to a Friedel-Crafts acetylation reaction in the presence of a saturated hydrocarbon solvent.Type: GrantFiled: March 16, 1993Date of Patent: July 4, 1995Assignee: Unilever Patent Holdings, BVInventors: Christopher P. Newman, Karen J. Rossiter, Terence L. Miller
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Patent number: 5395975Abstract: Polyacylated aromatic compounds of formula I ##STR1## where R.sup.1 is phenyl which is unsubstituted or has inert substituents or is .alpha.-halo-C.sub.1 -C.sub.6 -alkyl, it being possible for these radicals to be identical or different;R.sup.2 is C.sub.1 -C.sub.4 -alkyl;m is 2 or 3;n is 0 to 4, it being possible for the R.sup.2 substituents to be different when n>1,with the proviso that m+n.ltoreq.6, are prepared by reacting an acylaromatic compound of the formula II ##STR2## where p is 1 or 2, with a carbonyl halide of the formula III ##STR3## where X is halogen, in an amount appropriate for the desired degree of acylation, in the presence of Fe(II), Fe(III), Zn(II), Mo(VI), W(VI) or Sn(IV) compounds.Type: GrantFiled: December 1, 1993Date of Patent: March 7, 1995Assignee: BASF AktiengesellschaftInventors: Wolfgang Siegel, Jochen Schroeder
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Preparation of nitrobenzophenones, and a color-stable modification of a benzophenone-azopyridone dye
Patent number: 5364972Abstract: A process for preparing nitrobenzophenones by reaction of benzene or its derivatives with nitrobenzoyl chloride in the presence of a Lewis acid, a color-stable modification of 1,4-dimethyl-5-cyano-3-[4-(2,4-dimethylbenzoyl)phenylazo]-2-hydroxy-6-pyri done and its use for dyeing or printing synthetic fiber material are described.Type: GrantFiled: September 23, 1992Date of Patent: November 15, 1994Assignee: BASF AktiengesellschaftInventors: Helmut Degen, Norbert Zimmerman, Ralf Brueckmann, Gunther Lamm, Arno Lange, Helmut Reichelt -
Patent number: 5362715Abstract: The invention is directed to a mixture of acetylpolyalkylindanes and acetylpolyalkyltetralines obtainable by cycloalkylation of p-cymene and/or p,.alpha.-dimethylstyrene and/or 8-p-cymenyl halides and/or 8-p-cymenyl alcohol with a mixture of alkenes consisting of one or more methylbutene isomers and one or more dimethylbutene isomers, followed by acetylation of the intermediate mixture of polyalkylindanes and polyalkyltetralines.Type: GrantFiled: April 15, 1993Date of Patent: November 8, 1994Assignee: PFW Aroma Chemicals B.V.Inventors: Amnon M. Cohen, Frank E. Conboy, Willem Lenselink, Everardus A. Oostveen
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Patent number: 5360936Abstract: 1-Indanones of the formula IV or IVa ##STR1## in which R.sup.1 to R.sup.7 are preferably hydrogen or alkyl, or adjacent radicals R.sup.1 to R.sup.4 form a ring, are obtained in a one-step reaction by reacting a compound I ##STR2## with a compound of the formula II ##STR3## or with a compound of the formula (III) ##STR4## in anhydrous hydrogen fluoride and with boron trifluoride.Type: GrantFiled: September 10, 1993Date of Patent: November 1, 1994Assignee: Hoechst AktiengesellschaftInventors: Laurent Weisse, Heinz Strutz
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Patent number: 5349095Abstract: A process for preparing a substituted or unsubstituted 3- or 4-hydroxyalkylbenzocyclobutene compound comprises reducing a corresponding 3- or 4-formyl or ketobenzocyclobutene compound with a hydride at a temperature below that at which dimerization or oligomerization of the formyl- or ketobenzocycloutene compound or the thus-produced hydroxyalkylbenzocyclobutene compound is a significant side reaction, for a time sufficient to convert the formyl- or ketobenzocyclobutene compound to the hydroxyalkylbenzocyclobutene compound. In a two-step process, formylbenzocyclobutenes are prepared from bromobenzocyclobutenes in 90% yield or from benzocyclobutenes in a 70% yield, and then converted to hydroxymethylbenzocyclobutenes for an overall yield of about 85% from a bromobenzocyclobutene or of about 65% from a benzocyclobutene.Type: GrantFiled: November 25, 1992Date of Patent: September 20, 1994Assignee: The Dow Chemical CompanyInventors: P. J. Thomas, R. Garth Pews
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Patent number: 5329050Abstract: 1-Indanones of the formula IV or IVa ##STR1## in which R.sup.1 and R.sup.7 are preferably hydrogen or alkyl, or adjacent radicals R.sup.1 to R.sup.4 form a ring, are obtained in a one-step reaction by reacting a compound I ##STR2## with a compound of the formula II or a compound III ##STR3## in liquid hydrogen fluoride.Type: GrantFiled: April 27, 1993Date of Patent: July 12, 1994Assignee: Hoechst AktiengesellschaftInventors: Laurent Weisse, Jurgen Rohrmann, Frank Kuber, Heinz Strutz
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Patent number: 5300693Abstract: Process for producing 1,4-bis-(4-fluorbenzoyl)-benzol by reacting terephthaloyl chloride with fluorbenzol in the presence of aluminium chloride or aluminium bromide, characterized in that aluminium chloride or aluminium bromide is added in metered quantities to a mixture of terephthaloyl chloride and fluorbenzol at temperatures of approximately 25.degree. C. to approximately 68.degree. C. and the mixture is allowed to react at said temperatures.Type: GrantFiled: November 25, 1992Date of Patent: April 5, 1994Assignee: Hoechst AktiengesellschaftInventors: Walter Gilb, Georg Grotsch, Hans Schubert