Oxy Containing Reactant Patents (Class 568/347)
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Patent number: 4334098Abstract: Described is the compound trans, trans-.DELTA.-damascone and mixtures of trans, trans-.DELTA.-damascone and its isomer, cis, trans-.DELTA.-damascone is in a major proportion, a process for preparing same and processes for adding such trans, trans-.DELTA.-damascone or such mixtures containing high proportions of trans, trans-.DELTA.Type: GrantFiled: March 23, 1979Date of Patent: June 8, 1982Assignee: International Flavors & Fragrances Inc.Inventors: Braja D. Mookherjee, Robert W. Trenkle, Richard A. Wilson, Frederick L. Schmitt, Manfred H. Vock, Edward J. Granda, Joaquin Vinals, Jacob Kiwala, William L. Schreiber
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Patent number: 4330482Abstract: In the process for the production of a halogenoalkene of the formula ##STR1## in which R.sup.1 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aralkenyl or aryl radical or an optionally substituted heterocyclic radical,R.sup.2 represents a halogen atom, a cyano group, an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkenyl, aryl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl or aminocarbonyl radical or an optionally substituted heterocyclic radical, andX is a halogen atom,in which an .alpha.-hydroxy-phosphonic acid ester of the formula ##STR2## in which R.sup.3 each independently is an alkyl or phenyl radical, or the two radicals R.sup.3 together are an alkanediyl (alkylene) radical,is reacted with a phosphorus-containing olefinating agent of the formula ##STR3## in which Z.sup.1 is the phosphorus-containing radical ##STR4## R.sup.4 and R.sup.5 each independently is an alkyl, phenyl, alkoxy or phenoxy radical or together are an alkanedioxy radical, andR.Type: GrantFiled: December 18, 1980Date of Patent: May 18, 1982Assignee: Bayer AktiengesellschaftInventor: Hellmut Hoffmann
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Patent number: 4323711Abstract: A process for producing 3-(5-hydroxy-3-methyl-1,3-pentadienyl)-2,4,4-trimethyl-2-cyclohexen-1-one, an intermediate for canthaxanthin, by hydrogenation of 5-(2,6,6-trimethyl-3-oxo-cyclohexen-1-yl)-3-methyl-2-penten-4-yn-1-ol with zinc and a carboxylic acid.Type: GrantFiled: November 10, 1980Date of Patent: April 6, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Teodor Lukac, Erich Widmer, Reinhard Zell
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Patent number: 4318855Abstract: The instant invention provides a new and improved method of preparing .alpha.-hydroxycarbonyl compounds, particulary substituted cyclopent-2-en-2-ol-1-ones and substituted 3-hydroxy-2(5H)-furanones. The novel sequence involves a number of novel intermediates including substituted 2-cyanocyclopentanones, substituted 2-cyano-2-hydroxycyclopentanones, and 2-cyano-2-hydroxyvalero-.gamma.-lactones.Type: GrantFiled: January 24, 1980Date of Patent: March 9, 1982Assignee: Givaudan CorporationInventors: Ulrich Huber, Hans-Jakob Wild
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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: 4314072Abstract: 2-(2-Hydroxy-3-oxobutyl)-3,3-dimethylcyclopropanecarbaldehyde and certain derivatives thereof are useful intermediates for the preparation of dihalovinyl-type pyrethroid esters.Type: GrantFiled: November 23, 1979Date of Patent: February 2, 1982Assignee: Shell Oil CompanyInventor: Johannes L. M. Syrier
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Patent number: 4310701Abstract: A process is described for the preparation of alkyl and alkylene homologues of methyl dihydrojasmonatewhich incorporate the novel process step: ##STR1## In the above reaction sequence, X is chloro or bromo and R is C.sub.1 -C.sub.4 alkyl.Type: GrantFiled: November 13, 1980Date of Patent: January 12, 1982Assignee: International Flavors & Fragrances Inc.Inventors: Richard A. Wilson, Braja D. Mookherjee, John B. Hall, Gilbert Stork
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Patent number: 4308401Abstract: The present invention relates to novel compounds useful as fragrance materials which have the structure ##STR1## wherein the dashed line may be either a carbon-carbon single bond or a carbon-carbon double bond; R.sub.1, R.sub.2 and R.sub.3 are each the same or different and each represents hydrogen or methyl; and X is halogen. The invention also provides methods of preparing these compounds from readily available cyclohexene derivatives and fragrance compositions which include the compounds.Type: GrantFiled: December 22, 1980Date of Patent: December 29, 1981Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Philip A. Christenson, Robert Mack
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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: 4303674Abstract: A compound of formula (I): ##STR1## wherein the dotted line indicates an optional double bond and R is a hydrogen atom or a methyl group has topical anti-inflammatory activity.Type: GrantFiled: May 27, 1980Date of Patent: December 1, 1981Assignee: Beecham Group LimitedInventor: Alexander C. Goudie
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Patent number: 4298757Abstract: 2-(2,2-Dihalovinyl-3,3-dimethylcyclopropyl)vinyl alkanoates in which the alkanoate moiety contains from two to six carbon atoms are new chemical compounds useful as intermediates in the preparation of certain pyrethroid acids. The alkanoates are prepared by reacting 2-(2,2-dihalovinyl-3,3-dimethylcyclopropyl)ethanal with the appropriate alkanoic acid anhydride.Type: GrantFiled: July 9, 1979Date of Patent: November 3, 1981Assignee: Shell Oil CompanyInventors: Johannes Van Berkel, Hendrik C. Kelderman
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Patent number: 4296259Abstract: A new process for preparing 1-(3-oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-1,4-pentadien-3-ol, a intermediate for canthaxanthin, from hydroxy-.beta.-ionone.Type: GrantFiled: June 9, 1980Date of Patent: October 20, 1981Assignee: Hoffmann-La Roche Inc.Inventor: Urs Hengartner
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Patent number: 4292447Abstract: Described is a process for preparing hydrogenated derivatives of 2,6,6-trimethyl cyclohexene derivatives by means of treating said derivatives with hydrogen in the presence of a supported palladium catalyst such as palladium-on-calcium carbonate or palladium-on-barium sulfate in the presence of a quinoline activator. The resulting products are useful for their organoleptic properties as foodstuff flavorants and flavor enhancers, perfume composition ingredients, perfumed article ingredients and tobacco flavorants and flavor enhancers.Type: GrantFiled: December 15, 1978Date of Patent: September 29, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Robert W. Trenkle, Braja D. Mookherjee, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
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Patent number: 4288613Abstract: 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: GrantFiled: December 3, 1979Date of Patent: September 8, 1981Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 4282158Abstract: Derivatives of .alpha.,.beta.-unsaturated ketones having anticonvulsant activity and methods of their preparation from heterocyclic phosphonium salts and acyclic phosphoranes are disclosed.Type: GrantFiled: February 27, 1980Date of Patent: August 4, 1981Assignee: G. D. Searle & Co.Inventor: Richard A. Mueller
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Patent number: 4281204Abstract: The present invention relates to substituted spirocyclic derivatives having the general formula: ##STR1## wherein the dotted line represents 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, and R.sub.6 are each the same or different, hydrogen or lower alkyl, wherein Z is one of the following: ##STR2## wherein R.sub.7 is either hydrogen or lower alkyl, wherein R.sub.8 and R.sub.9 are each lower alkyl; their methods of preparation and their use as odor-modifying ingredients in perfumes and perfumed products, and as flavor-modifying ingredients in the flavoring of foodstuffs and tobacco products.Type: GrantFiled: October 5, 1979Date of Patent: July 28, 1981Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Robert G. Eilerman
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Patent number: 4277625Abstract: New process for the preparation of muscone, a valuable macrocyclic musky perfume ingredient. The process makes use of an .alpha.,.omega.-dialdehyde as starting material.Type: GrantFiled: November 20, 1979Date of Patent: July 7, 1981Assignee: Firmenich SAInventors: Karl-Heinrich Schulte-Elte, Arnold Hauser, Gunther Ohloff
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Patent number: 4268445Abstract: The preparation of bicyclic enol-ethers (I) ##STR1## (where n is from 3 to 12, and R.sup.1, R.sup.2 and R.sup.3 may be H or C.sub.1 --C.sub.4 -alkyl) by free radical adduct formation of CHR.sup.1 =CR.sup.2 --CHR.sup.3 --O--R.sup.4 (III)(where R.sup.4 is tert.-butyl, tetrahydrofuran-2-yl or tetrahydropyran-2-yl) with a cyclic ketone (IV) ##STR2## followed by acid-catalyzed cyclization, and novel compounds II ##STR3## The compounds (I) and (II) are intermediates for the synthesis of musk-like fragrances.Type: GrantFiled: January 31, 1980Date of Patent: May 19, 1981Assignee: BASF AktiengesellschaftInventors: Rudolf Kropp, Frank Thoemel, Axel Nuerrenbach, Werner Hoffman, Franz Wenisch, Hartwig Fuchs
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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: 4254280Abstract: 2-(2-Hydroxy-3-oxobutyl)-3,3-dimethylcyclopropanecarbaldehyde and certain derivatives thereof, such as 1-[2-(2,2-dihalovinyl)-3,3-dimethylcyclopropyl]-3-oxo-2-butyl acetate, are useful intermediates for the preparation of dihalovinyl-type pyrethroid esters.Type: GrantFiled: November 23, 1979Date of Patent: March 3, 1981Assignee: Shell Oil CompanyInventor: Johannes Syrier
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Patent number: 4250332Abstract: Described is a process for preparing .beta.-damascone starting with 2,6,6-trimethyl cyclohex-2-enone according to the reaction sequence: ##STR1## wherein Z is hydrogen, MgX', Li, Na or K; Y is MgX', Li, Na or K; X' is Cl, Br or I; R is C.sub.1 -C.sub.3 lower alkyl such as methyl, ethyl, n-propyl or i-propyl; X is Cl, Br or I. Also described are the organoleptic uses of the compound having the structure: ##STR2## in augmenting or enhancing the taste or aroma of a consumable material, e.g., foodstuff, chewing gum, medicinal product, chewing tobacco, smoking tobacco, perfume, perfumed article (e.g., drier-added fabric softener articles and solid or liquid anionic, cationic or nonionic detergents) and cologne.Type: GrantFiled: October 26, 1979Date of Patent: February 10, 1981Assignee: International Flavors & Fragrances Inc.Inventors: Robert W. Trenkle, Braja D. Mookherjee, John B. Hall, Robin Kasper, Manfred H. Vock, Ronald Schreck, Edward J. Granda, Joaquin F. Vinals
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Patent number: 4217252Abstract: Described is a process for augmenting or enhancing the aroma of a perfume composition as well as perfume and cologne compositions containing a mixture consisting essentially of compounds having the structures: ##STR1## and wherein the mixture contains 30% of the compounds having the structures; ##STR2## and 60% of the compound having the structure: ##STR3##Type: GrantFiled: May 15, 1979Date of Patent: August 12, 1980Assignee: International Flavors & Fragrances Inc.Inventors: Robert W. Trenkle, Braja D. Mookherjee, Robin Kasper, Manfred H. Vock, Joaquin Vinals, Jacob Kiwala, Frederick L. Schmitt
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Patent number: 4212827Abstract: Process for the manufacture of canthaxanthin by oxidizing .beta.-carotene, retro-dehydro-carotene or echinenone with a salt of chloric or bromic acid in the presence of a catalyst and of an inert diluent or solvent.Type: GrantFiled: October 13, 1977Date of Patent: July 15, 1980Assignee: BASF AktiengesellschaftInventors: Joachim Paust, Joachim Schneider, Hagen Jaedicke
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Patent number: 4210553Abstract: Described is a process for augmenting or enhancing the aroma of solid or liquid anionic, cationic or nonionic detergent compositions comprising adding to a solid or liquid anionic, cationic or nonionic detergent base, an aroma augmenting or enhancing quantity of at least one of the compounds having a structure: ##STR1## whereby sweet, floral, fruity, rose-like, minty/camphoraceous aromas with floral, hay-like, musty backgrounds and tobacco nuances are augmented, enhanced or imparted.Type: GrantFiled: May 15, 1979Date of Patent: July 1, 1980Assignee: International Flavors & Fragrances Inc.Inventors: Robert W. Trenkle, Braja D. Mookherjee, Robin Kasper, Manfred H. Vock, Joaquin Vinals, Jacob Kiwala, Frederick L. Schmitt
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Patent number: 4209450Abstract: A process for introducing an allyl-positioned carbonyl group into a 2,6,6-trimethylcyclohexene ring which carries a polyenyl radical in the 1-position, by oxidizing the ring with a halogen(V)-oxyacid or a salt of such an acid, and the new oxo compounds obtainable by the said process, which may be used as dyes for foodstuffs or cosmetics. The oxidation is carried out in the presence of a catalyst and of an inert diluent or solvent, in an acid medium. Suitable catalysts are bromine and iodine and the oxides of elements of groups Va, VIa, VIIa and VIII of the periodic table.Type: GrantFiled: January 10, 1978Date of Patent: June 24, 1980Assignee: BASK AktiengesellschaftInventors: Hagen Jaedicke, Joachim Paust
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Patent number: 4204073Abstract: A process for producing trimethyl oxo or hydroxy substituted cycopentenone food coloring agents including intermediates in this process.Type: GrantFiled: April 6, 1979Date of Patent: May 20, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Frank Kienzle
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Patent number: 4202822Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner