Reactant Contains -coo- Group Patents (Class 568/314)
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Patent number: 4554363Abstract: Process for the preparation of bicyclic ketones containing blocked hydroxy groups, of general Formula I ##STR1## wherein R.sub.1 is the residues --CH.sub.2 OR.sub.2 wherein R.sub.2 means benzyl, dimethyl-tert-butylsilyl, diphenyl-tert-butylsilyl, dimethylphenylsilyl, tribenzylsilyl, or tetrahydropyranyl, ##STR2## with R.sub.2 having the meanings given above, R.sub.4 meaning hydrogen or methyl, and R.sub.5 meaning a straight-chain or branched-chain, saturated or unsaturated alkyl residue which can contain fluorine, chlorine, 1,2-methylene, 1,1-trimethylene, or methoxy substitutents, or a CH.sub.2 --X-Aryl residue with X meaning CH.sub.2 or O and Aryl meaning phenyl or a heterocyclic residue, which residues can be substituted by methyl, methoxy, fluorine, chlorine, bromine, or trifluoromethyl, or ##STR3## with the meanings for R.sub.2, R.sub.4, and R.sub.5 as indicated above, and R.sub.3 having the meanings set forth for R.sub.2, it being possible for R.sub.3 to be identical to R.sub.2 or different from R.sub.Type: GrantFiled: June 23, 1983Date of Patent: November 19, 1985Assignee: Schering AktiengesellschaftInventor: Helmut Vorbrueggen
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Patent number: 4528400Abstract: 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: GrantFiled: November 20, 1981Date of Patent: July 9, 1985Assignee: SDS Biotech CorporationInventors: Richard L. Cryberg, Russell M. Bimber
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Patent number: 4504671Abstract: Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.Type: GrantFiled: October 15, 1982Date of Patent: March 12, 1985Assignee: PPG Industries, Inc.Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
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Patent number: 4496767Abstract: A novel process for preparing 2-cyclopentenones of the formula: ##STR1## wherein R.sub.1 is hydrogen, alkyl or alkenyl and R.sub.2 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl, which comprises esterifying a mixture of a 3-hydroxy-4-cyclopentenone of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are each as defined above and a 4-hydroxy-2-cyclopentenone of the formulas: ##STR3## wherein R.sub.1 and R.sub.2 are each as defined above with an aliphatic carboxylic acid to give a mixture of the 4-hydroxy-2-cyclopentenone (III) and the cyclopentenone ester of the formula: ##STR4## wherein R.sub.1 and R.sub.2 are each as defined above and R is hydrogen or C.sub.1 -C.sub.4 alkyl and subjecting the resulting mixture to reduction.Type: GrantFiled: October 18, 1983Date of Patent: January 29, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Tadashi Katsura
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Patent number: 4482745Abstract: The present invention provides a novel method for the preparation of 1,3-diphenyl-1,3-propanedione.Type: GrantFiled: November 2, 1983Date of Patent: November 13, 1984Assignee: American Cyanamid CompanyInventor: Donald R. Maulding
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Patent number: 4480132Abstract: Disclosed is a process for the preparation of .alpha.,.beta.-unsaturated ketones containing a 2-oxopropylidene moiety by the reaction of an aldehyde with a 2,2-dialkyl-4-methyl-6-keto-1,3-dioxene in the presence of a catalytic amount of certain metallic halides.Type: GrantFiled: November 21, 1983Date of Patent: October 30, 1984Assignee: Eastman Kodak CompanyInventors: William T. Brown, Robert M. Simons
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Patent number: 4446078Abstract: A process for the preparation of .alpha.,.alpha.-difluoroalkoxy or .alpha.,.alpha.-difluoroalkylthiophenyl ketones, in which a polyhaloalkoxybenzene or a polyhaloalkylthiobenzene is reacted with a carboxylic acid, a precursor or a derivative of this acid in the presence of boron trifluoride in such an amount that the absolute pressure of the boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having phytosanitary (e.g., herbicidal) or pharmaceutical activity.Type: GrantFiled: June 28, 1982Date of Patent: May 1, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4424166Abstract: In the preparation of a 1,1-dihalogenoalkene of the formula ##STR1## in which R.sup.1 is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain, andX.sup.1 and X.sup.2 each independently is a halogen atom,wherein a carbonyl compound of the formula ##STR2## is reacted with a trihalogenoacetate of the formula ##STR3## in which X.sup.3 is a halogen atom, andM.sup..sym. is an alkali metal ion or one equivalent of an alkaline earth metal ion,in the presence of an approximately equimolar amount of a phosphorus-containing compound, the improvement which comprises employing as said phosphorus-containing compound a phosphorous acid trialkyl ester or a phosphorous acid triamide and effecting the reaction at a temperature between about 0.Type: GrantFiled: February 23, 1981Date of Patent: January 3, 1984Assignee: Bayer AktiengesellschaftInventors: Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
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Patent number: 4422870Abstract: 2-Aryl-1, 3-cyclohexanedione enol ester compounds exhibit outstanding miticidal,mite ovicidal and herbicidal activity.Type: GrantFiled: March 28, 1977Date of Patent: December 27, 1983Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4362670Abstract: Carbon acids are allylated by contacting with an allyl carbonate in the presence of a palladium catalyst.Type: GrantFiled: September 3, 1981Date of Patent: December 7, 1982Assignee: The Dow Chemical CompanyInventor: Edmund P. Woo
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Patent number: 4358460Abstract: 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: GrantFiled: March 30, 1981Date of Patent: November 9, 1982Assignee: Beiersdorf AktiengesellschaftInventor: Erich Cohnen
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Patent number: 4357278Abstract: What are disclosed are a multi-step synthesis for the preparation of 9(11)-dehydroestrone 3-methyl ether from 2-methyl,4-methoxy benzaldehyde; 1-(4-methoxy-2-methyl-(phenyl)-3-(1-methyl-2-oxo-5-t-vinyl-cyclopent-r-yl) -propane-1-one, an intermediate in said synthesis; and a method for the preparation of 3-vinylcyclopentanone from 2-vinylcyclopropane-1,1-dicarboxylic acid.Type: GrantFiled: April 10, 1981Date of Patent: November 2, 1982Assignee: Hoechst AktiengesellschaftInventors: Gerhard Quinkert, Wolf-Dietrich Weber, Ulrich Schwartz
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Patent number: 4315032Abstract: A novel 7-hydroxyprostaglandin E.sub.1, or a stereoisomer thereof, or a protected derivative thereof, having the following formula: ##STR1## wherein R.sup.8 represents H, CH.sub.3 or C.sub.2 H.sub.5, R.sup.9 represents H or CH.sub.3, R.sup.10 and R.sup.11 are identical or different, and each represents H, tetrahydropyranyl or t-butyldimethylsilyl. Also provided is a process for producing an adjacently disubstituted ketone including the above compounds, i.e. 7-oxoprostaglandin, etc. which comprises reacting an .alpha.,.beta.-unsaturated carbonyl compound with a cuprous salt and an organolithium compound in an aprotic inert organic medium in the presence of trialkylphosphine, the amounts of said cuprous salt and said organolithium compound being substantially equimolar, and reacting the product with a protected acetal derivative of an organic carbonyl compound or an aldehyde in the presence of a Lewis acid, if necessary, followed by reacting the product with a proton donor.Type: GrantFiled: May 14, 1980Date of Patent: February 9, 1982Assignee: Teitin LimitedInventors: Ryoji Noyori, Masaaki Suzuki, Seizi Kurozumi
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Patent number: 4283348Abstract: 2-Aryl-1,3-cyclopentanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal and acaricidal activity.Type: GrantFiled: September 26, 1979Date of Patent: August 11, 1981Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4276225Abstract: A carboxylic acid ester activated in .alpha.-position by a keto, ester or nitrile group, i.e. of the formula ##STR1## where X is COOR.sup.4, COR.sup.5 or CN, and the several R's can have various meanings but only R.sup.1 and R.sup.2 can be hydrogen, is decarbalkoxylated by heating in the presence of a salt, e.g. sodium chloride, and a phosphorus-containing solvent such as a phospholine oxide, phospholane oxide or phosphetane oxide of the formulas ##STR2## wherein a-k and R can have varied definitions. Water is present either at the outset or end of the reaction before product separation. The reaction proceeds smoothly and in good yields.Type: GrantFiled: August 8, 1977Date of Patent: June 30, 1981Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hellmut Hoffmann
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Patent number: 4270004Abstract: The present invention relates to a process for the preparation of 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl)butan-2-one and to certain compounds for use in that process.British patent specification No. 1,474,377 discloses inter alia that 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl)butan-2-one possesses useful anti-inflammatory activity. A particularly favored process has now been discovered that can be used to produce 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl)butan-2-one in particularly good yield.The present invention provides a process for the preparation of 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl)butan-2-one which process comprises the hydrogenation of a compound of the formula (I): ##STR1## wherein Ar is a 6-methoxy-2-naphthyl group; X and Y are each hydrogen atoms or together represent a second bond between the carbon atoms to which they are attached; and R is a group such that --CO.sub.2 R represents an ester group convertible by hydrogenation to a CO.sub.2 H group.Type: GrantFiled: October 11, 1979Date of Patent: May 26, 1981Assignee: Beecham Group LimitedInventors: Carl J. Rose, David Miller
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Patent number: 4256657Abstract: 2-Aryl-1,3-cyclohexanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal, miticidal and mite ovicidal activity.Type: GrantFiled: January 22, 1980Date of Patent: March 17, 1981Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4256658Abstract: 2-Aryl-1,3-cyclohexanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal, miticidal and mite ovicidal activity.Type: GrantFiled: January 22, 1980Date of Patent: March 17, 1981Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4252739Abstract: 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: GrantFiled: August 20, 1979Date of Patent: February 24, 1981Assignee: Emery Industries, Inc.Inventors: Richard G. Fayter, Jr., John F. White, Eugene G. Harris
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Patent number: 4247709Abstract: The present invention relates to a process for the preparation of 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl)butan-2-one and to certain compounds for use in that process.British Pat. Spec. No. 1,474,377 discloses inter alia that 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl) butan-2-one possesses useful anti-inflammatory activity. A particularly favored process has now been discovered that can be used to produce 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl) butan-2-one in particularly good yield.The present invention provides a process for the preparation of 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl)butan-2-one which process comprises the hydrogenation of a compound of the formula (I): ##STR1## wherein Ar is a 6-methoxy-2-naphthyl group; X and Y are each hydrogen atoms or together represent a second bond between the carbon atoms to which they are attached; and R is a group such that --CO.sub.2 R represents an ester group convertible by hydrogenation to a CO.sub.2 H group.Type: GrantFiled: December 26, 1978Date of Patent: January 27, 1981Assignee: Beecham Group LimitedInventors: Carl J. Rose, David Miller
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Patent number: 4230862Abstract: Derivatives of 3-phenyl-4-aroyl-1,2-dihydronaphthalenes and 1-aroyl-2-phenylnaphthalenes are useful both as antifertility agents and in suppressing the growth of mammary tumors.Type: GrantFiled: August 3, 1978Date of Patent: October 28, 1980Assignee: Eli Lilly and CompanyInventors: Tulio Suarez, C. David Jones
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Patent number: 4221741Abstract: This invention provides a process for the preparation of 4-(6'-methoxy-2'naphthyl)-butan-2-one, which process comprises the hydrogenation of 4-(6' methoxy-2'-naphthyl)-4-hydroxy-but-3-en-2-one.Type: GrantFiled: January 19, 1979Date of Patent: September 9, 1980Assignee: Beecham Group LimitedInventor: Laramie M. Gaster
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Patent number: 4212828Abstract: A process for asymmetric synthesis of optically active 2-alkanoyl-1,2,3,4-tetrahydro-2-naphthol compounds of the formula: ##STR1## from L-proline or its ester and the following carboxylic acid of the formula: ##STR2## or its reactive derivative through the following intermediary compounds in order: ##STR3##Type: GrantFiled: November 24, 1978Date of Patent: July 15, 1980Assignee: Sumitomo Chemical Company, LimitedInventors: Kenji Koga, Shiro Terashima