Nitrogen Containing Material Utilized Patents (Class 568/436)
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Patent number: 5169958Abstract: A process for the preparation of .alpha.,.beta.-unsaturated carbonyl compounds of the formula I ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -alkoxy or aryloxy,R.sup.2 is aryl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl and/or halogen andR.sup.3 is tetrahydrofuranyl or aryl which is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl and/or halogen, which comprises reacting 3-amino-2-propen-1-ones of the formula II ##STR2## where R.sup.1 and R.sup.2 have the abovementioned meanings, and R.sup.4 and R.sup.5 are, independently of one another, hydrogen, C.sub.1 -C.sub.10 -alkyl or aryl, with a magnesium halide of the formula IIIR.sup.3 --Mg--Y (III)where Y is halogen, at from -20.degree. to 100.degree. C., and novel .alpha.,.beta.-unsaturated carbonyl compounds and novel 3-amino-2-propen-1-ones are described.Type: GrantFiled: October 1, 1991Date of Patent: December 8, 1992Assignee: BASF AktiengesellschaftInventors: Heinz Isak, Norbert Goetz, Thomas Kuekenhoehner
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Patent number: 5162577Abstract: A novel process for the lithiation of 1,3-bis(trifluoro-methyl)benzene in a solvent is described, said process comprising carrying out the lithiation with the lithium salt of an amine of the general formulaR.sup.1 R.sup.2 NH Iwherein R.sup.1 and R.sup.2 are secondary or tertiary lower alkyl or secondary or tertiary lower alkyl substituted by a lower alkyl or lower cycloalkyl or lower cycloaklyl substituted by a lower alkyl, or R.sup.1 and R.sup.2 taken together form a C.sub.6-14 -alkylene group in which the two carbon atoms linked with the nitrogen atom are secondary or tertiary and are separated from each other by 2 to 4 carbon atoms.The solution of the lithiated 1,3-bis(trifluoromethyl)-benzene obtained can be reacted with an electrophile which is suitable for the substitution of lethiated benzene derivatives, whereby a compound of the formula ##STR1## wherein R.sup.3 signifies the residue of an electrophile which is suitable for the substitution of lithiated benzene derivatives, is obtained.Type: GrantFiled: February 1, 1991Date of Patent: November 10, 1992Assignee: Hoffmann-La Roche Inc.Inventor: Raffaello Masciadri
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Patent number: 5155280Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, an alkali metal nitrosodisulfonate, a non-basic polar solvent and an oxidant, for about eight hours or less at a temperature in the range of from about 10.degree. C. to about 20.degree. C. and thereafter separating out the aldehyde.Type: GrantFiled: September 30, 1991Date of Patent: October 13, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5155279Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid and a solvent, in the absence of an oxidant at a temperature in the range of from about -10.degree. C. to about 60.degree. C. and thereafter separating out the aldehyde.Type: GrantFiled: October 18, 1991Date of Patent: October 13, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5155277Abstract: A process for converting tertiary amine N-oxides to aldehydes by reacting tertiary amine N-oxides in the presence of a catalytic quantity of a vanadium containing compound.Type: GrantFiled: June 11, 1991Date of Patent: October 13, 1992Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Pierre Chabardes, Serge Henrot, Claude Mercier
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Patent number: 5149882Abstract: 2-chloro-5-nitrobenzaldehyde or an acetal thereof is isolated from a mixture of isomers thereof at a temperature of from -10.degree. to +140.degree. C., by suspending the mixture of isomers in a solvent or solvent mixture.Type: GrantFiled: June 4, 1991Date of Patent: September 22, 1992Inventors: Bernd Schaefer, Wolfgang Freund, Gernot Reissenweber
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Patent number: 5124487Abstract: p-Trifluoromethyl benzaldehydes are prepared by the catalytic reduction reaction of p-trifluoromethyl benzonitriles with hydrogen in an aqueous formic acid media in the presence of a nickel/aluminum alloy catalyst.Type: GrantFiled: August 5, 1991Date of Patent: June 23, 1992Assignee: Occidental Chemical CorporationInventors: James J. Maul, Garra C. Lester, Henry C. Lin
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Patent number: 5082976Abstract: Benzaldehydes of the formula ##STR1## can be obtained by reaction of substituted .beta.-amino-styrenes of the formula ##STR2## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.8, R.sup.9, R.sup.10, m, n and o have the scope of meaning indicated in the description, with oxygen in the presence of a Cu compound in the solution of an aprotic polar solvent at 0.degree.-120.degree. C.Type: GrantFiled: October 25, 1990Date of Patent: January 21, 1992Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Helmut Kraus
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Patent number: 4845305Abstract: 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: GrantFiled: July 7, 1988Date of Patent: July 4, 1989Assignee: National Starch and Chemical CorporationInventor: Eric A. Meier
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Patent number: 4766251Abstract: 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 functionality is preserved by formation of a corresponding Schiff's base or acetal, and its subsequent regeneration by treatment with aqueous acid.Type: GrantFiled: August 11, 1987Date of Patent: August 23, 1988Assignee: National Starch and Chemical CorporationInventors: Robert D. Rossi, Steven P. Fenelli
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Patent number: 4647446Abstract: A method for detecting the blood flow in animals, particularly in the brain, is provided wherein a detectable amount of a novel radioactive compound of the formula I is administered to one animal: ##STR1## wherein R.sub.1 and R.sub.2 are independently alkyl of 1 to 6 carbon atoms or benzyl;R.sub.3 is alkyl of 1 to 6 carbon atoms, benzyl, cyclopropylalkyl of 4 to 6 carbon atoms, or cyanoalkyl of 2 to 6 carbon atoms;R.sub.4 is hydrogen, benzyl or alkyl of 1 to 6 carbon atoms;with the provisos that R.sub.4 is not isopropyl and when R.sub.4 is methyl, R.sub.3 is not benzyl;and X is a radioactive halogen.Type: GrantFiled: May 9, 1985Date of Patent: March 3, 1987Assignee: The Regents of the University of CaliforniaInventors: Thornton W. Sargent, III, Alexander T. Shulgin, Chester A. Mathis
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Patent number: 4645852Abstract: In an improved process of converting a 1,2-epoxy-2-phenylbutane or a 1,2-epoxy-2-phenylpentane to a 2-hydroxy-2-phenylbutylsulfonate, sulfamate, or halide, or the corresponding 2-hydroxy-2-phenylpentyl compound, respectively, by the reaction at about 40.degree. to 120.degree. C. in the presence of an organic solvent of the requisite epoxybutane or epoxypentane with a proton source and a nucleophile. The proton source can be a free strong acid such as a sulfonic, sulfamic acid, or hydrohalide acid, or the proton source can be derived from an equilibrium system comprising a free strong acid and weak base in equilibrium with the respective deprotonated strong acid and protonated weak base. The process is carried out in one step with reduction or avoidance of aldehyde formation by rearrangement of the epoxyalkane.Type: GrantFiled: September 16, 1985Date of Patent: February 24, 1987Assignee: The Dow Chemical CompanyInventors: Lennon H. McKendry, Richard C. Krauss
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Patent number: 4590281Abstract: Provided is a process for preparing an aldehyde or aldehydes represented by the following formula (III), characterized in that a diaryliodonium salt represented by the following formula (I) is reacted with an unsaturated alcohol represented by the following formula (II) in a solvent containing a base in the presence of a transition metal catalyst at a temperature in the range of room temperature to 100.degree. C.:[Ar.sub.1 --I.sup..sym. --Ar.sub.2 ] X.sup..crclbar. (I)CHR.sub.1 .dbd.CR.sub.2 --CH.sub.2 OH (II)Ar.sub.3 --CHR.sub.1 --CHR.sub.2 --CHO (III)wherein Ar.sub.1 and Ar.sub.2, which may be alike or different, are each an aryl group which may have a substituent group or groups, X.sup..crclbar. is a counter ion which is inert to the above reaction, Ar.sub.3 is the same aryl group as Ar.sub.1 or Ar.sub.2, and R.sub.1 and R.sub.2 are each hydrogen atom or an alkyl group of C.sub.1 to C.sub.12.Type: GrantFiled: March 7, 1984Date of Patent: May 20, 1986Assignee: Nippon Petrochemicals CompanyInventors: Yasuo Yamazaki, Takehiko Suzuki
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Patent number: 4588844Abstract: Aromatic aldehydes are prepared by formylating the corresponding aromatic compounds with urotropine in the presence of hydrogen fluoride. By the described process certain new aromatic aldehydes can be prepared.Type: GrantFiled: February 1, 1984Date of Patent: May 13, 1986Assignee: Bayer AktiengesellschaftInventors: Ernst Kysela, Erich Klauke
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Patent number: 4584410Abstract: In a Reimer-Tiemann reaction for the preparation of a mixture of two hydroxybenzaldehydes (i.e., salicylaldehyde and p-hydroxybenzaldehyde) by reacting phenol with chloroform and an aqueous alkali solution in a heterogeneous system, the two hydroxybenzaldehydes can be prepared in a controlled formation ratio, yield and reaction rate depending upon the conditions used when the reaction is carried out in the presence of a phase transfer catalyst selected from the group consisting of a cationic type phase transfer catalyst, an amphoteric type phase transfer catalyst and an anionic type phase transfer catalyst.Type: GrantFiled: November 13, 1984Date of Patent: April 22, 1986Assignee: Sumitomo Chemical Co., Ltd.Inventors: Kazuhiko Hamada, Gohfu Suzukamo, Fujio Masuko, Makoto Nakamura
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Patent number: 4578462Abstract: The manufacture of optically active bifunctional compounds of the general formula ##STR1## wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R.sup.1 represents a group of the formula ##STR2## or --CH.sub.2 --CH.dbd.NR.sup.2 in which R.sup.2 and R.sup.3 represent lower alkyl or cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom represent a heterocyclic ring,by isomerizing compounds of the general formula ##STR3## wherein R, R.sup.2 and R.sup.3 have the above significance and R.sup.3 can additionally signify hydrogen,is described.The compounds of formula I are potential intermediates in the manufacture of, inter alia, natural vitamin E and natural vitamin K.sub.1.Type: GrantFiled: August 22, 1983Date of Patent: March 25, 1986Assignee: Hoffmann-La Roche Inc.Inventors: Hans-Jurgen Hansen, Rudolf Schmid, Max Schmid
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Patent number: 4568772Abstract: This invention discloses a novel process for producing p-t-butyl-.alpha.-methyldihydrocinnamaldehyde which comprises converting the .alpha.-methyldihydrocinnamaldehyde to an enamine, oxazolidine or a Schiff's base, reacting said derivative with a tertiary butyl cation, and then removing the protective group.Type: GrantFiled: September 14, 1983Date of Patent: February 4, 1986Assignee: Givaudan CorporationInventors: Albert Gabbai, Karl-Fred De Polo
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Patent number: 4558163Abstract: This disclosure describes a novel process for the preparation of 9,10-anthracenedicarboxaldehyde by the oxidation of 9,10-bis(chloromethyl)anthracene.Type: GrantFiled: July 19, 1984Date of Patent: December 10, 1985Assignee: American Cyanamid CompanyInventor: Steven L. Peake
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Patent number: 4540826Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.Type: GrantFiled: August 12, 1983Date of Patent: September 10, 1985Assignee: Phillips Petroleum CompanyInventors: Dennis S. Banasiak, Jim D. Byers
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Patent number: 4500721Abstract: A process for producing benzaldehydes by catalytic reduction of benzonitriles in the presence of an acid using a Raney nickel catalyst pretreated with a copper salt is disclosed.Type: GrantFiled: February 23, 1983Date of Patent: February 19, 1985Assignee: Sumitomo Chemical Company LimitedInventors: Hiroshi Yamachika, Hirotoshi Nakanishi
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Patent number: 4465865Abstract: A method of preparing terephthalic aldehyde or isophthalic aldehyde from p-xylene or m-xylene, which comprises chlorinating the side chain or p or m xylene to a chlorination degree of 2.5 to 3.5, and thereafter contacting the so-chlorinated product with hexamethylenetetramine in aqueous solution at elevated temperature whereby the corresponding aldehyde is obtained.Type: GrantFiled: February 22, 1982Date of Patent: August 14, 1984Assignee: Dynamit Nobel AktiengesellschaftInventors: Fritz Englander, Klaus-Dieter Steffen
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Method for producing aldehydes and ketones using 2,2'-bipyridinium chlorochromate as oxidizing agent
Patent number: 4426534Abstract: 2,2'-bipyridinium chlorochromate has been found to be an effective oxidizing agent, particularly for the conversion of primary or secondary alcohols to their respective aldehydes or ketones.Type: GrantFiled: July 26, 1982Date of Patent: January 17, 1984Assignee: Thiokol CorporationInventor: Frank S. Guziec, Jr. -
Patent number: 4424389Abstract: A process for producing chroman, a compound of the formula, ##STR1## or an optically active compound thereof wherein R.sub.2, R.sub.3 and R.sub.4 are each a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, which comprises reacting a compound of the formula, ##STR2## or an optically active compound thereof wherein A is an aryl group and R.sub.5 is a C.sub.1 -C.sub.4 alkyl group, with a compound of the formula, ##STR3## wherein R.sub.1 is a C.sub.1 -C.sub.3 alkyl group, X is a halogen atom and R.sub.2, R.sub.3 and R.sub.4 are as defined above, to obtain a compound of the formula, ##STR4## or an optically active compound thereof wherein A, R.sub.1, R.sub.2, R.sub.3 and R.sub.Type: GrantFiled: April 12, 1982Date of Patent: January 3, 1984Assignee: Sumitomo Chemical Company, LimitedInventor: Yoji Sakito
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Patent number: 4408077Abstract: A process and intermediates for preparing 6-(lower alkoxy)-5-(trifluoromethyl)-1-naphthalenecarboxylic acid derivatives are disclosed. The derivatives are useful for preparing aldose reductase inhibitors. With reference to the process, 1,1,1-trifluoro-5-(2-methylphenyl)-2,3-pentadione 3-oxime is cyclized to give a key intermediate 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone oxime; and 3,4-dihydro-1-hydroxy-5-methyl-1-(trifluoromethyl)-2(1H)-naphthalenone is aromatized to 5-methyl-1-(trifluoromethyl)-2-naphthalenol with a dehydrating agent.Type: GrantFiled: November 13, 1981Date of Patent: October 4, 1983Assignee: Ayerst, McKeena & Harrison, Inc.Inventors: Kazimir Sestanj, Steven Fung, Nedumparambil A. Abraham, Francesco Bellini
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Patent number: 4383949Abstract: A process for the preparation of a 3-bromo-4-fluorobenzaldehyde acetal of the formula ##STR1## in which R.sup.1 is methyl or ethyl,which comprises reacting a 3-bromo-4-fluoro-benzoic acid halide with ammonia to form 3-bromo-4-fluoro-benzoic acid amide, dehydrating said amide to form 3-bromo-4-fluoro-benzonitrile, reacting the nitrile with formic acid in the presence of a catalyst at a temperature between about 0.degree. and 150.degree. C. to form 3-bromo-4-fluorobenzaldehyde, and reacting said aldehyde with R.sup.1 OH or a derivative thereof capable of forming an acetal. The amide and nitrile are new compounds. The acetals are known intermediates in the synthesis of pyrethroid-like insecticides.Type: GrantFiled: June 26, 1981Date of Patent: May 17, 1983Assignee: Bayer AktiengesellschaftInventors: Fritz Maurer, Hans-Jochem Riebel, Uwe Priesnitz, Erich Klauke
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Patent number: 4383122Abstract: An optically active or racemic .alpha.-hydroxyaldehyde represented by the general formula (2), ##STR1## wherein R.sub.1 represents a C.sub.6 -C.sub.14 aryl group, C.sub.1 -C.sub.10 alkyl group, C.sub.3 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R.sub.2 represents a C.sub.1 -C.sub.10 alkyl group, C.sub.2 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, C.sub.6 -C.sub.14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), ##STR2## (wherein A represents a C.sub.6 -C.sub.14 aryl group or a C.sub.1 -C.sub.4 alkyl or alkoxy group- or halogen-substituted C.sub.6 -C.sub.14 aryl group and R.sub.Type: GrantFiled: April 27, 1981Date of Patent: May 10, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
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Patent number: 4337346Abstract: An optically active or racemic .alpha.-hydroxyaldehyde represented by the general formula (2), ##STR1## wherein R.sub.1 represents a C.sub.6 -C.sub.14 aryl group, C.sub.1 -C.sub.10 alkyl group, C.sub.3 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R.sub.2 represents a C.sub.1 -C.sub.10 alkyl group, C.sub.2 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7-C.sub.14 aralkyl group, C.sub.6 -C.sub.14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), ##STR2## (wherein A represents a C.sub.6 -C.sub.14 aryl group or a C.sub.1 -C.sub.4 alkyl or alkoxy group- or halogen-substituted C.sub.6 -C.sub.14 aryl group and R.sub.Type: GrantFiled: October 30, 1979Date of Patent: June 29, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
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Patent number: 4335052Abstract: A process for the preparation of Benzaldehydes substituted in the nucleus is disclosed by oxidation of the corresponding benzyl halides. The process is performed in the presence of water using aminoxides of tertiary amines.Type: GrantFiled: November 24, 1980Date of Patent: June 15, 1982Assignee: Dynamit Nobel AktiengesellschaftInventors: Gunther Bernhardt, Egon-Norbert Petersen, Gerhard Daum
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Patent number: 4328374Abstract: A process for the production of aromatic dialdehydes which comprises reacting xylene chloride selected from the group consisting of .alpha.,.alpha.,.alpha.'-trichloroxylene alone, or a mixture of .alpha.,.alpha.,.alpha.'-trichloroxylene and .alpha.,.alpha.'-dichloroxylene, a mixture of .alpha.,.alpha.,.alpha.'-trichloroxylene and .alpha.,.alpha.,.alpha.',.alpha.'-tetrachloroxylene and a mixture of .alpha.,.alpha.,.alpha.'-trichloroxylene, .alpha.,.alpha.'-dichloroxylene and .alpha.,.alpha.,.alpha.',.alpha.'-tetrachloroxylene with nitric acid.Type: GrantFiled: July 7, 1980Date of Patent: May 4, 1982Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Shigeo Yoshinaka, Masaharu Doya
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Patent number: 4322563Abstract: Substituted biphenyl-2-carboxaldehydes are prepared in good yield by reacting palladium complexes of substituted benzaldehyde aniline Schiff bases with substituted phenylmagnesium bromides in the presence of at least six, preferably eight, molar equivalents of triphenylphosphine.Type: GrantFiled: February 11, 1981Date of Patent: March 30, 1982Assignee: Merck & Co., Inc.Inventor: William F. Hoffman
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Patent number: 4321412Abstract: In a process for the preparation of aromatic monoaldehydes by reacting monochlorinated methylaromatics with hexamethylenetetramine by a Sommelet reaction, the improvement that in place of pure chloromethylaromatics the chlorination mixtures produced by photochlorination of the methylaromatics are employed and are treated with hexamethylenetetramine without prior working up, after which the Sommelet reaction is allowed to take place.Type: GrantFiled: October 15, 1980Date of Patent: March 23, 1982Assignee: BASF AktiengesellschaftInventors: Werner Schoch, Michael Kroener, Rudi Widder
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Patent number: 4287368Abstract: A new radioenzymatic assay for catecholamines utilizing the catechol-0-methyl transferase transfer of a methyl group from a labeled methyl donor to the catecholamines followed by isolation of the 0-methylated(.sup.3 H)catecholamine and the subsequent measurement of radioactivity.Type: GrantFiled: February 26, 1980Date of Patent: September 1, 1981Assignee: The Upjohn CompanyInventors: Garland A. Johnson, Jacob D. Peuler
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Patent number: 4206152Abstract: The present invention provides a process for the production of unsubstituted or substituted o-phthalaldehydes by hydrolysis of .alpha.,.alpha., .alpha.',.alpha.'-tetrahalogeno-o-xylenes with a carboxylate in an aqueous medium in the presence of a phase transfer catalyst and an organic base.Type: GrantFiled: December 21, 1978Date of Patent: June 3, 1980Assignee: Ciba-Geigy CorporationInventor: Jacques Gosteli