Reactant Contains -coo- Group Patents (Class 568/346)
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Patent number: 4371460Abstract: Kentones of the formula ##STR1## wherein each of the symbols R.sup.1, R.sup.2, and R.sup.3 identical or different, represent a hydrogen atom or a lower alkyl radical containing 1 to 3 carbon atoms are disclosed useful as perfuming agents and in the preparation of perfume products.Type: GrantFiled: December 22, 1981Date of Patent: February 1, 1983Assignee: Firmenich SAInventors: Ferdinand Naf, Rene Decorzant, Karl H. Schulte-Elte
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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: 4340753Abstract: A method is provided for oxidatively cleaving .alpha.,.beta.-unsaturated cyclic ketones, such as isophorone, with an oxidizing agent, for example, ozone, and thereafter recovering the resulting keto acid. In instances where ozone is used, an aqueous hydroperoxide and phase transfer catalyst can be used to recover the keto acid. Dione cyclics, for example, dimedone, can be obtained by direct dehydration of the keto acid.Type: GrantFiled: September 2, 1980Date of Patent: July 20, 1982Assignee: General Electric CompanyInventor: James A. Cella
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Patent number: 4336201Abstract: A process for the preparation of an electrically conductive polyene, wherein a polyene which contains one or more chain members of the formula where R is hydrogen or methyl, and which contains a total of not less than seven aliphatic double bonds, is treated, in the absence of moisture and of oxygen, with a strong Lewis acid having a pk.sub.a of from -10 to +4, or with an alkali metal.Type: GrantFiled: November 3, 1980Date of Patent: June 22, 1982Assignee: BASF AktiengesellschaftInventors: Franz Feichtmayr, Herbert Naarmann, Joachim Paust, Klaus Penzien
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Patent number: 4335253Abstract: A process for the preparation of dihalovinyl compounds of the formula ##STR1## wherein each Hal is fluorine, chlorine or bromine, R.sup.1 is an optionally substituted hydrocarbyl group, R.sup.2 is a methyl group or a hydrogen atom, or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form cycloalkylidene group, which process comprises treating a trihalo compound of the formula ##STR2## wherein Hal, R.sup.1 and R.sup.2 have the above meanings and R.sup.3 is a hydrogen atom or ##STR3## in which M is an alkali atom, with PHal.sub.3.Type: GrantFiled: May 22, 1981Date of Patent: June 15, 1982Assignee: Shell Oil CompanyInventor: Petrus A. Kramer
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Patent number: 4335261Abstract: A macrocyclic ketone having a 15- to 17-membered ring is produced from an .alpha.,.omega.-long chain dicarboxylic acid ester by the Dieckmann condensation reaction, followed by hydrolysis/decarboxylation reaction and then purification. The macrocyclic ketone is purified by subjecting the ketone to steam distillation in the presence of a non-volatile base.Type: GrantFiled: June 17, 1981Date of Patent: June 15, 1982Assignee: Daicel Chemical Industries, Ltd.Inventor: Yoichiro Ueda
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Patent number: 4326996Abstract: The present invention relates to substituted cyclohexane derivatives having the structure: ##STR1## wherein the dotted line may be a carbon-carbon double bond or a carbon-carbon single bond; wherein R.sub.1,R.sub.2,R.sub.3, R.sub.4,R.sub.5,R.sub.6,R.sub.7 and R.sub.8 may be hydrogen or lower alkyl; wherein Z may be any of the following: ##STR2## wherein R.sub.9 may be hydrogen or lower alkyl; and wherein R.sub.10 and R.sub.11 are lower alkyl. This invention also provides methods of preparing and using the compounds as odor-modifying ingredients in perfumes and perfumed products, and as flavor-modifying ingredients in foodstuffs and tobacco products.Type: GrantFiled: January 30, 1980Date of Patent: April 27, 1982Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Robert G. Eilerman
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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: 4310705Abstract: An improved process for the preparation of higher unsaturated ketones, such as geranylacetone and farnesylacetone, by reacting a .beta.,.gamma.-unsaturated alcohol and an alkyl acetoacetate at an elevated temperature in the presence of an organic aluminum compound, with elimination, and removal, of the alcohol derived from the alkyl acetoacetate in a reactor system carrying a fractionating column. The improvement in the purity, yield, and especially space-time yield of the product is achieved by starting from an alcohol having a higher boiling point than that of the alkyl acetoacetate used, carrying out the reaction in the presence of a small amount of an inert liquid which has a boiling point between that of the alkyl acetoacetate and the alcohol to be eliminated therefrom, and ensuring that the temperature at the bottom of the fractionating column is only slightly higher than the boiling point of the added liquid, under the prevailing pressure.Type: GrantFiled: June 26, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventors: Axel Nissen, Gerd Kaibel, Otto Woerz, Lothar Arnold, Manfred Braun, Walter Rebafka
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Patent number: 4307251Abstract: A novel process for the preparation of (R) or (S) 2-allyl-3-methyl-4-hydroxy-2-cyclopentene-1-one comprising reacting a boron halide with an ester of a chiral carboxylic acid of the formula ##STR1## where A is organic group of a chiral carboxylic acid and (R) or (S) 2-allyl-3-methyl-4-hydroxy-2-cyclopentene-1-one and treating the reaction mixture with water to obtain allethrolone with the same configuration of the starting ester in high yields without undesired by-products produced in known methods.Type: GrantFiled: June 2, 1980Date of Patent: December 22, 1981Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4307243Abstract: Conversion of esters (R.sup.1)(R.sup.2)C(C Hal.sub.3)OX, X being-P Hal.sub.2, --C(O)OR.sup.3 or ##STR1## R.sup.1, R.sup.3 and R.sup.4 being optionally substituted hydrocarbyl groups and R.sup.2 methyl or hydrogen, with zinc in acetic acid gives a very high yield of a dihalovinyl compound (R.sup.1)(R.sup.2)C.dbd.C Hal.sub.2, e.g., of the ethyl ester of the parent acid of pyrethroid insecticides.Type: GrantFiled: March 25, 1980Date of Patent: December 22, 1981Assignee: Shell Oil CompanyInventors: Petrus A. Kramer, Pieter A. Verbrugge
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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: 4267376Abstract: A compound having the general formula ##STR1## wherein R.sup.1 is a lower alkyl group, R.sup.2 is hydrogen or a lower alkyl group and Y is a protected hydroxyl group, for example, (.+-.)-3.beta.-tert.butoxy-2,3,3a,4,5,7,8,9,9a.beta.,9b.alpha.-decahydro-3 a.beta.-methyl-6-(3-butenyl)-1H-benz(e)inden-7-one, which is an intermediate for steroids, is prepared by dehydrative cyclization of a compound of the general formula ##STR2## wherein the symbols of R.sup.1, Y and R.sup.2 are same as defined above.Type: GrantFiled: August 30, 1979Date of Patent: May 12, 1981Assignee: Takeda Chemical Industries, Ltd.Inventor: Jiro Tsuji
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Patent number: 4259518Abstract: The invention concerns new 3-methyl-5-keto-.alpha.,.omega.-alkene-dioic acids of the general formula ##STR1## wherein the double bond is in one of the positions indicated by the broken lines,R.sub.1 and R.sub.2 independently of one another are a hydrogen atom or a C.sub.1 -C.sub.4 -alkyl group,x is an integer from 9 to 11 andy and z independently of one another are 1 or 2, but cannot both be 1;a process for their preparation and their use for the preparation of macrocyclic .beta.-methyl ketones which are valuable fragrances.Type: GrantFiled: August 30, 1979Date of Patent: March 31, 1981Assignee: Bayer AktiengesellschaftInventors: Kurt Bauer, Detlef Hagena
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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: 4220799Abstract: The known condensation reaction of lower alkanoylacetic acid lower alkyl esters with aldehydes catalyzed by amines proceeds safe and in high yields if the amineis an aliphatic tertiary amine. The products are precursors of aromatic amines.Type: GrantFiled: December 1, 1977Date of Patent: September 2, 1980Assignee: Hoechst AktiengesellschaftInventors: Rudiger Berthold, Bernhard Mees, Hartmut Heise