Preparing Esters From Aldehydes Patents (Class 560/238)
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Patent number: 5089659Abstract: E7/Z9 -alkadien-1-ols which may be protected at the hydroxy group are prepared by subjecting a 7-hydroxyheptenal to a Wittig reaction with a phosphorylide to give an acetal compound which is converted by further Wittig reaction with a phosphorylide to an E7/Z9 -alkadienol.Type: GrantFiled: May 19, 1989Date of Patent: February 18, 1992Assignee: BASF AktiengesellschaftInventors: Christiane Brueckner, Ernst Buschmann, Wolfgang Mackenroth, Walter Himmele, Heinz Eckhardt
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Patent number: 4883906Abstract: A process for producing and refining trisubstituted glycol monoesters, e.g., 2,2,4-trimethyl-1,3-pentanediol monoester. The improvement resides in immediately distilling the crude condensation product mixture as it leaves the reactor before it has cooled or had any contact with added water.Type: GrantFiled: November 25, 1987Date of Patent: November 28, 1989Assignee: Union Carbide CorporationInventors: John N. Argyropoulos, Edmond J. Derderian, Brian T. Keen, Timothy G. Bumgardner
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Patent number: 4877898Abstract: A process for the one step esterification of aldehydes and alcohols comprises the steps of combining an aldehyde with an alcohol, in the presence of oxygen and in contact with a catalyst having the general formulaPdTe.sub.a Zn.sub.d E.sub.ewhereE is one or more metals from the group consisting of group IA, IIA, IVA, VIIB or VIII metals, As or Sb; anda, d and e are from about 0 to 3 with the proviso that at least d or e.noteq.0.Type: GrantFiled: June 12, 1986Date of Patent: October 31, 1989Assignee: The Standard Oil CompanyInventors: Christos Paparizos, Wilfrid G. Shaw, James L. Callahan
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Patent number: 4873362Abstract: 2-Substituted 4-acyloxy-2-butenals of the general formula I ##STR1## where R.sup.1 is alkyl of 1 to 12 carbon atoms which may be substituted by cycloalphatic, aromatic or heterocyclic radicals, by alkenyl or alkynyl or by hydroxyl, ether, thioether, acetoxy acyl, alkylamino, carboxyl or carbalkoxy, and R.sup.2 is acyloxy, are prepared by reacting a monosubstituted acetaldehyde of the general formula II ##STR2## where R.sup.2 has the abovementioned meaning, with an aldehyde of the general formula III ##STR3## where R.sup.1 has the abovementioned meaning, in the presence of a linear or cyclic secondary amine and of an organic acid at from 20.degree. to 100.degree. C.Type: GrantFiled: November 2, 1987Date of Patent: October 10, 1989Assignee: BASF AktiengesellschaftInventors: Franz Merger, Rolf Fischer, Hans Horler
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Patent number: 4843170Abstract: A process is disclosed for producing vinyl acetate from methanol, carbon monoxide and hydrogen which comprises the following five steps:(a) methanol is hydrocarbonylated in a hydrocarbonylation zone to produce ethanol, acetaldehyde, methyl acetate and dimethylacetal, and the products are separated in a separation zone;(b) methyl acetate is carbonylated in a carbonylation zone to produce acetic anhydride;(c) the acetaldehyde and dimethylacetal produced in the step (a) and the acetic anhydride produced in the step (b) are converted to ethylidene diacetate and methyl acetate; (d) the ethylidene diacetate produced in the step (c) is thermally decomposed to vinyl acetate and acetic acid, and the products are separated in a separation zone; and(e) the methyl acetate produced and separated in the step (a), (c) or (d) is supplied to the carbonylation step (b).Type: GrantFiled: February 15, 1983Date of Patent: June 27, 1989Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomiya Isshiki, Yasuhiko Kijima, Akira Ito, Kenji Ishii
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Patent number: 4841097Abstract: Disclosed herein are dialkanoyloxybenzylidene dialkanoate represented by the formula ##STR1## wherein X.sup.1 and X.sup.2 represent respectively alkanoyloxy group and a pharmaceutical composition in dosage unit form which comprises a dosage effective for the treatment of inflammatory disease of the dialkanoyloxybenzylidene dialkanoate as an active ingredient thereof.Type: GrantFiled: April 13, 1988Date of Patent: June 20, 1989Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Hitoshi Takita, Fumihiko Kimura, Sakuo Noda, Yutaka Mukaida, Toyohiko Nitta, Hidetoshi Kobayashi
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Patent number: 4751307Abstract: Disclosed are improved Wittig reaction processes wherein the Wittig reaction is conducted in an anisole containing solvent.Type: GrantFiled: February 27, 1987Date of Patent: June 14, 1988Assignee: Mallinckrodt, Inc.Inventor: Carl R. White
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Patent number: 4723036Abstract: There is provided a process for producing propylene glycol monoacetate which comprises the steps of(I) hydroformylating vinyl acetate with a gaseous mixture of hydrogen and carbon monoxide in an organic solvent in the presence of a substantially water-insoluble rhodium complex and a tri-substituted phosphine to form .alpha.-acetoxypropionaldehyde,(II) subjecting at least part of the reaction mixture obtained in step (I) to extraction with an aqueous medium to obtain an aqueous layer containing .alpha.-acetoxypropionaldehyde and an extraction residue containing the catalyst components, and recycling the extraction residue to the hydroformylation step (I),(III) contacting the aqueous layer containing .alpha.-acetoxypropionaldehyde obtained in step (II) with a carboxylic acid ester of general formula (A)C.sub.l H.sub.2l+1 COOC.sub.m H.sub.2m+1 (A)wherein l is an integer of 0 to 4; m is an integer of 1 to 5; and the sum of l and m is 3 to 5, or a dicarboxylic acid ester of general formula (B)ROOC(CH.sub.2).sub.Type: GrantFiled: September 30, 1982Date of Patent: February 2, 1988Assignee: Kuraray Company, Ltd.Inventors: Takanori Kitamura, Masuhiko Tamura
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Patent number: 4618704Abstract: Acyloxy-2-butenes of the formula ##STR1## where R.sup.1, R.sup.3 and R.sup.4 are each hydrogen or alkyl of 1 to 5 carbon atoms, R.sup.2 is alkyl of 1 to 5 carbon atoms, R.sup.5 is hydrogen, alkyl of 1 to 5 carbon atoms or R.sup.6 --CO--O, and R.sup.6 and R.sup.7 are each hydrogen, alkyl of 1 to 5 carbon atoms, phenyl or cyclohexyl, the preparation of these acyloxy-2-butenes by reaction of 1-acyloxy-1,3-butadienes of the formula ##STR2## with carboxylic acids of the formula R.sup.7 --COOH and oxygen at 50.degree.-180.degree. C. in the presence of catalysts containing palladium or platinum, and the use of the compounds of the formula I, where R.sup.1, R.sup.3, R.sup.4 and R.sup.5 are hydrogen, R.sup.2 and R.sup.6 are methyl and R.sup.7 is methyl or ethyl, for the preparation of 4-acyloxytiglic aldehydes.Type: GrantFiled: April 3, 1979Date of Patent: October 21, 1986Assignee: BASF AktiengesellschaftInventors: Hans-Martin Weitz, Rolf Fischer
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Patent number: 4593115Abstract: An 1-Iodoalkyl acylate, which is useful as the raw material for esterification of cephalosporins, penicillins, etc. is prepared in a high degree of purity and in high yield by (1) allowing a carboxylic acid iodide to react with an aldehyde, or (2) allowing a carboxylic acid chloride to react with a salt of hydriodic acid and then allowing the resulting product to react with an aldehyde, or (3) by simultaneously allowing a carboxylic acid chloride, a salt of hydriodic acid and an aldehyde to react with one another.Type: GrantFiled: November 21, 1984Date of Patent: June 3, 1986Assignee: Takeda Chemical Industries, Ltd.Inventors: Akio Miyake, Masayoshi Yamaoka
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Patent number: 4568782Abstract: Disclosed is the vapor phase cyclodehydration of an aldehyde or ketone over a solid Lewis acid as catalyst to make indene or a substituted indene according to the equation: ##STR1##Type: GrantFiled: June 17, 1985Date of Patent: February 4, 1986Assignee: The Standard Oil CompanyInventors: Marco Pagnotta, Mark C. Cesa, James D. Burrington
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Patent number: 4520125Abstract: Catalysts for the preparation of carboxylates from an aldehyde and an alkanol in the presence of oxygen, which contain palladium and lead as active components, these being present on a carrier containing zinc oxide, and the palladium being applied as a palladium salt in a solution containing hydrochloric acid and then being liberated by reduction, and whose carrier consists solely of zinc oxide, are particularly active and selective.Type: GrantFiled: February 23, 1984Date of Patent: May 28, 1985Assignee: BASF AktiengesellschaftInventors: Karl Baer, Peter Bassler, Gerd Duembgen, Gerd Fouquet, Richard Krabetz, Franz Merger, Friedbert Nees
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Patent number: 4518797Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO,--C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: March 15, 1979Date of Patent: May 21, 1985Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4518796Abstract: A method for preparing a carboxylic ester by reacting an aldehyde with an alcohol in the presence of oxygen with a catalyst, characterized in that the catalyst is a solid catalyst comprising palladium and bismuth, which may form an intermetallic compound, and which catalyst may comprise an alkali metal compound or an alkaline earth metal compound. The aforesaid catalyst avoids decomposition reactions simultaneously with the desired reaction, and therefore, the desired compound can be obtained in a high yield.Type: GrantFiled: May 13, 1980Date of Patent: May 21, 1985Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Atsushi Aoshima, Yoshio Suzuki, Setsuo Yamamatsu, Tatsuo Yamaguchi
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Patent number: 4493801Abstract: Tertiary alcohols are prepared by oxidizing tertiary aldehydes with oxygen at elevated temperatures.The tertiary alcohols prepared in this way are valuable and versatile intermediates for dyes, drugs and crop protection agents and are used, for example, in the preparation of agrochemicals.Type: GrantFiled: November 2, 1981Date of Patent: January 15, 1985Assignee: BASF AktiengesellschaftInventors: Franz Merger, Gerhard Nestler
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Patent number: 4440946Abstract: This invention is a process for producing a carboxylate ester which involves contacting mixtures of alcohol and aldehyde in vapor phase with a reduced silver-cadmium-zinc-zirconium catalyst composition.Type: GrantFiled: July 26, 1982Date of Patent: April 3, 1984Assignee: Celanese CorporationInventors: Richard H. Summerville, deceased, James E. Summerville, Jr., administrator
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Patent number: 4399302Abstract: The invention is directed to 4-methylmercapto-2-cacetoxy-butyraldehyde of the formula ##STR1## and a process for its production by hydroformylating 3-methylmercapto-1-acetoxy-propene-1 of the formula ##STR2## 4-methylmercapto-2-acetoxy-butyraldehyde can be used as an intermediate product for the production of 4-methylmercapto-2-hydroxy-butyric acid, the hydroxy analogue of methionine.Type: GrantFiled: February 25, 1982Date of Patent: August 16, 1983Assignee: Degussa AktiengesellschaftInventors: Kleemann, Axel, Rudolf Fahnenstich, Marc Samson
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Patent number: 4380663Abstract: A process is provided for the preparation of practically formic acid-free acetic acid by oxidation of acetaldehyde in the liquid phase with oxygen or oxygen-containing gases in the presence of mixtures of cobalt, nickel and manganese salts as catalysts.Type: GrantFiled: October 20, 1977Date of Patent: April 19, 1983Assignee: Hoechst AktiengesellschaftInventors: Gunter Roscher, Helmut Schaum, Heinz Schmitz
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Patent number: 4353832Abstract: A process for the production of carboxyl compounds such as caprolactones, in which the corresponding carbonyl compounds are oxidized with hydrogen peroxide in the presence of a catalyst in a substantially anhydrous liquid medium. The water formed by the reaction and any water introduced into the reaction mixture are removed from the reaction mixture.Type: GrantFiled: June 5, 1980Date of Patent: October 12, 1982Assignee: INTEROX (Societe Anonyme)Inventors: Andre Lecloux, Claude Declerck, Franz Legrand
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Patent number: 4322355Abstract: An improvement in the reaction of olefin with aldehyde, and optionally, carboxylic acid, in the liquid phase in the presence of a catalytically effective amount of strong acid to provide a 1,3-difunctional compound or a mixture of 1,3-difunctional compounds is provided by carrying out the aforesaid reaction in the further presence of a co-catalyst selected from the group consisting of antimony oxide, bismuth oxide, antimony salt, bismuth salt and mixtures thereof.Type: GrantFiled: April 15, 1980Date of Patent: March 30, 1982Assignee: National Distillers & Chemical Corp.Inventors: David Horvitz, William D. Baugh
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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: 4301084Abstract: In a process for the preparation of a carboxylic acid ester of .beta.-formyl-crotyl alcohol by rearrangement of the corresponding carboxylic acid ester of 2-formyl-2-hydroxy-but-3-ene or of an acetal or acylate thereof in the presence of copper or a copper compound, followed, where relevant, by hydrolytic cleavage of the acetal or acylate, more especially in the preparation of 4,4-dimethoxy-3-methyl-crotyl acetate, the yield is improved by carrying out the rearrangement in the presence of copper (I) chloride as the catalyst and ensuring that low-boiling by-products formed during the rearrangement are removed.The products are of great importance as starting materials for an industrial synthesis of vitamin A and its derivatives.Type: GrantFiled: August 31, 1979Date of Patent: November 17, 1981Assignee: BASF AktiengesellschaftInventors: Harald Laas, Axel Nissen, Bernd Meissner
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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: 4277633Abstract: The palladium complex disclosed herein is bis[tri(ortho-tolyl)phosphine] :palladium which is produced by reacting a palladium salt with tri(ortho-tolyl)phosphine and reducing the resultant bis[tri(ortho-tolyl)phosphine] palladium salt with an alcoholic alkali. This complex is useful as a catalyst for the production of 1,3-diene oligomers.Type: GrantFiled: July 12, 1979Date of Patent: July 7, 1981Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Satoru Enomoto, Hisayuki Wada, Sadao Nishita, Yutaka Mukaida, Mikiro Yanaka, Hitoshi Takita
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Patent number: 4273934Abstract: 3-Hydroxy-2,2,4-trimethylpentyl isobutyrate is prepared by reaction of isobutyraldehyde in the presence of an alkaline earth metal hydroxide and of carboxylic acids or the corresponding salts, under specific conditions in respect of reaction time and proportion and concentration of the hydroxide suspension. The product is a starting material for the preparation of dyes, pesticides, adhesives and surface coatings.Type: GrantFiled: April 17, 1979Date of Patent: June 16, 1981Assignee: BASF AktiengesellschaftInventors: Franz Merger, Hans-Juergen Foerster
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Patent number: 4263443Abstract: Hydrocarbons and esters and/or acids are produced by heating aldehydes in the presence of an alcohol or an alcohol equivalent and in the presence of an iodine or bromine moiety and a rhodium or iridium catalyst.Type: GrantFiled: November 22, 1978Date of Patent: April 21, 1981Assignee: Halcon Research and Development Corp.Inventor: John F. White
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Patent number: 4258207Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: March 15, 1979Date of Patent: March 24, 1981Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4258205Abstract: New 2,2-dimethylcyclopropanecarbaldehyde dimethyl acetal derivatives of the formula ##STR1## wherein X is --CH.sub.2 OC(O)CH.sub.3, --CH.sub.2 OH, or --CHO are useful chemical intermediates for the preparation of pesticidally active cyclopropanecarboxylates.Type: GrantFiled: December 4, 1978Date of Patent: March 24, 1981Assignee: Shell Oil CompanyInventors: Johannes Van Berkel, Hendrik C. Kelderman
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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: 4249019Abstract: A carboxylic ester is produced in one step in a high yield and with a high selectivity by reacting an aldehyde with an alcohol in the presence of oxygen by using a catalyst comprising (I) palladium, (II) at least one compound selected from the group consisting of lead compounds, thallium compounds and mercury compounds and (III) at least one compound selected from the group consisting of alkali metal compounds and alkaline earth metal compounds.Type: GrantFiled: November 13, 1978Date of Patent: February 3, 1981Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Nobuhiro Tamura, Yohei Fukuoka, Setsuo Yamamatsu, Yoshio Suzuki, Ryoichi Mitsui, Tadayuki Ibuki
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Patent number: 4229592Abstract: The compound of the formula ##STR1## has been found to be an important and practical intermediate with the proper stereo-isomerism for the preparation of numerous prostaglandin derivatives. It can easily be converted to 4.alpha.-acetoxy-2-cyclopentenone by a variety of processes.Type: GrantFiled: February 6, 1978Date of Patent: October 21, 1980Assignee: Kansas University Endowment AssociationInventors: Lester A. Mitscher, George W. Clark, III, Paul B. Hudson
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Patent number: 4225726Abstract: This invention relates to an improved method for the catalyzed condensation of aldehydes in the liquid phase to form 1,3-glycol monoesters utilizing tin metal or a tin oxide catalyst. Condensation can be visualized as an aldol condensation followed by a Tischenko reaction between the aldol and a third molecule of aldehyde. In its simplest form the condensation can be illustrated by the following general formula ##STR1## R or R.sup.1 =Hydrogen or alkyl group of 1 to 20 carbon atoms or aromatic groups. R and R.sup.1 can also be part of a cyclic system.Type: GrantFiled: May 23, 1979Date of Patent: September 30, 1980Assignee: Eastman Kodak CompanyInventors: Don L. Morris, Anthony W. McCollum
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Patent number: 4214099Abstract: A new synthesis of key prostaglandin precursors and intermediates employed in their preparation. The novel synthetic sequence of this invention is shorter and more efficient than those previously employed to prepare to key intermediate.Type: GrantFiled: June 22, 1978Date of Patent: July 22, 1980Assignee: Pfizer Inc.Inventors: Elias J. Corey, Jasjit S. Bindra, Thomas K. Schaaf
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Patent number: 4175204Abstract: E-4-acetoxy-2-methyl-2-butenal is prepared by: (1) preparation of an intermediate allylic halide from isoprene; and (2) reaction of the allylic halide with dimethyl sulfoxide in the presence of a non-nucleophilic base to form the desired product.Type: GrantFiled: January 8, 1979Date of Patent: November 20, 1979Inventor: James H. Babler
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Patent number: 4133836Abstract: A process for the manufacture of acetals by reacting aliphatic aldehydes with aliphatic alcohols, especially olefinically unsaturated aldehydes and allyl alcohols, in the presence of a distillable acid, especially nitric acid, using a rectifying column as the reaction vessel. The products may be used as starting materials for plastics, active substances, scents and vitamins.Type: GrantFiled: May 31, 1977Date of Patent: January 9, 1979Assignee: BASF AktiengesellschaftInventors: Axel Nissen, Gerd Kaibel
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Patent number: 4124619Abstract: Preparation of carboxylic acid esters of .gamma.-hydroxy-tiglic-aldehyde from bismonocarboxylic acid esters of but-2-en-1,4-diol via 1,4-diacetoxy-2-formyl butane including intermediates in this synthesis.Type: GrantFiled: March 23, 1977Date of Patent: November 7, 1978Assignee: Hoffmann-La Roche Inc.Inventors: Peter Fitton, Harold Moffet
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Patent number: 4118406Abstract: A process for preparing cis-olefins of the formula ##STR1## where R ia alkyl or alkenyl and R.sup.1 is alkyl and alkenyl, both optionally substituted by hydroxy, carbalkoxy or acyloxy, which comprises an ylide solution of the compound R--CH.sub.2 --P.sup..sym. (C.sub.6 H.sub.5).sub.3 Br.sup..crclbar. in hexaalkyl phosphoric acid traimide and adding an aldehyde of the formula R.sup.1 --CHO.Type: GrantFiled: August 8, 1977Date of Patent: October 3, 1978Assignee: Hoechst AktiengesellschaftInventors: Hans Jurgen Bestmann, Werner Theo Stransky, Otto Vostrowsky
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Patent number: 4100110Abstract: Novel compounds of use in perfumery are obtained by performing a Prins reaction on isolongifolene. They include novel primary and secondary alcohols, their esters and the corresponding aldehydes and ketones.Type: GrantFiled: August 11, 1975Date of Patent: July 11, 1978Assignee: Bush Boake Allen LimitedInventors: Hifzur Rahman Ansari, Neville Unwin, Horst Richard Wagner
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Patent number: 4087435Abstract: Novel 8-aza-9-dioxothiaprostanoic acid compounds, their salts, and derivatives, are prepared from ethyl 7-(3-hydroxymethyl-2-isothiazolidinyl)-5-heptynoate S,S-dioxide by first hydrogenating the triple bond over a Lindlar catalyst, followed by mild oxidation, to produce the corresponding 3-formyl compound, which is condensed with the ylide prepared from dimethyl-(2-oxoheptyl)phosphonate to produce the .alpha.,.beta.-unsaturated ketone, followed by reduction to the corresponding carbinol, and ester hydrolysis. The compounds are useful especially for the treatment of patients with poorly functioning kidneys, as hypotensives, or as platelet aggregation inhibitors.Type: GrantFiled: February 17, 1977Date of Patent: May 2, 1978Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., James H. Jones, John B. Bicking
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Patent number: 4072709Abstract: Lactic acid is synthesized by a process in which a vinyl ester is hydroformylated to an .alpha.-substituted propionaldehyde by reacting the vinyl ester with carbon monoxide and hydrogen in the presence of a hydroformylation catalyst and by further converting the .alpha.-substituted carbonyl intermediate via oxidation and hydrolysis to lactic acid.A preferred embodiment of the invention utilizes vinyl acetate as the feed.Type: GrantFiled: May 27, 1975Date of Patent: February 7, 1978Assignee: Monsanto CompanyInventor: Harold B. Tinker
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Patent number: 4069258Abstract: Cyclopentene derivatives (I) ##STR1## where R.sup.1 is isopropyl or isopropenyl, R.sup.2 is alkyl of 1 to 3 carbon atoms, X is --CHO, a dialkyl acetal or 1,2- or 1,3-alkylene acetal thereof where the acetal radical is of 2 to 6 carbon atoms, --CH.sub.2 OH or --CH.sub.2 OCOR.sup.3 where R.sup.3 is hydrogen or alkyl or alkenyl of up to 3 carbon atoms. The manufacture of I from the corresponding halomethyl cyclopentenes and aldehydes R.sup.2 --CH(CH.sub.3)--CHO in the presence of a base and a quaternary ammonium salt, followed if desired by acetalization or conversion of the --CHO group to the --CH.sub.2 OH or --CH.sub.2 O--CO--R.sup.3 groups. The compounds are useful as fragrance materials.Type: GrantFiled: March 15, 1976Date of Patent: January 17, 1978Assignee: BASF AktiengesellschaftInventors: Werner Hoffmann, Karl VON Fraunberg
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Patent number: 4069385Abstract: In the preparation of olefin derivatives having an ester group at the allylic position (hereinafter referred to as "allylic ester(s)") which comprises reacting an olefin having at least one hydrogen atom at the allylic position and which will produce an allylic ester having an asymmetric carbon atom with an organic peroxide in the presence of a copper catalyst, a method for producing optically active allylic esters characterized by using, as the copper catalyst, an optically active copper complex derived from an optically active compound selected from the group consisting of Schiff's bases of the formula: ##STR1## and amino acids of the formula: ##STR2## wherein R.sub.0 is an optically active alkyl, cycloalkyl, aralkyl or aryl group which may contain an unsaturated bond and/or a substituent having a hetero atom, X and Y are each a hydrogen atom, an alkyl, cycloalkyl, aralkyl or aryl group, or a substituent having a hetero atom, R.sub.1 and R.sub.Type: GrantFiled: June 3, 1976Date of Patent: January 17, 1978Assignee: Sumitomo Chemical Company, LimitedInventors: Masashi Araki, Tsuneyuki Nagase
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Patent number: 4049682Abstract: Described are processes for preparing enol esters having the generic structure: ##STR1## (which structure is intended to cover both the "cis" and the "trans" isomers thereof) wherein R.sub.1 is C.sub.1 -C.sub.11 alkyl, and R.sub.4 is hydrogen or methyl, produced by one of the following processes:I. Reacting beta-ionone or a homologue thereof with a peracid;Ii. Reacting an enol acetate formed by process (i) (when R.sub.1 is methyl and R.sub.4 is hydrogen) with an alkanoic acid anhydride or an acyl halide, to form another enol ester;Iii. Reacting beta-cyclohomocitral having the formula: ##STR2## with a lower alkanoic acid anhydride or an acyl halide.Type: GrantFiled: September 15, 1976Date of Patent: September 20, 1977Assignee: International Flavors & Fragrances Inc.Inventors: Alan Owen Pittet, Erich Manfred Klaiber, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals
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Patent number: 4048195Abstract: Total synthesis of known progestationally active steroidal materials. The steroids can be synthesized depending on the particular starting reactants selected by employing as intermediates bicyclic compounds of the formula ##STR1## WHEREIN M IS AN INTEGER HAVING A VALUE OF 1 TO 2; R.sub.4 is hydrogen or lower alkyl; Z is lower alkylenedioxy, CH(OR.sub.2) and carbonyl; R.sub.8 when taken alone is hydrogen, R.sub.9 when taken alone is lower alkoxy-carbonyl, aryloxy-carbonyl, lower cycloalkyloxy-carbonyl, carbonyl-halide, hydrogen, carboxy, formyl and methylene-X, where X is a leaving group and when taken together are methylene; with the proviso that when Z is carbonyl R.sub.8 when taken alone is hydrogen; R.sub.9 when taken alone is carbonyl halide, hydrogen, carboxy, formyl and methylene-X where X is a leaving group and when taken together are methylene and R.sub.Type: GrantFiled: July 14, 1976Date of Patent: September 13, 1977Assignee: Hoffmann-La Roche Inc.Inventor: Zoltan George Hajos