Preparing Esters From Aldehydes Patents (Class 560/238)
  • Patent number: 5089659
    Abstract: 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: Grant
    Filed: May 19, 1989
    Date of Patent: February 18, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Christiane Brueckner, Ernst Buschmann, Wolfgang Mackenroth, Walter Himmele, Heinz Eckhardt
  • Patent number: 4883906
    Abstract: 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: Grant
    Filed: November 25, 1987
    Date of Patent: November 28, 1989
    Assignee: Union Carbide Corporation
    Inventors: John N. Argyropoulos, Edmond J. Derderian, Brian T. Keen, Timothy G. Bumgardner
  • Patent number: 4877898
    Abstract: 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: Grant
    Filed: June 12, 1986
    Date of Patent: October 31, 1989
    Assignee: The Standard Oil Company
    Inventors: Christos Paparizos, Wilfrid G. Shaw, James L. Callahan
  • Patent number: 4873362
    Abstract: 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: Grant
    Filed: November 2, 1987
    Date of Patent: October 10, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Rolf Fischer, Hans Horler
  • Patent number: 4843170
    Abstract: 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: Grant
    Filed: February 15, 1983
    Date of Patent: June 27, 1989
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tomiya Isshiki, Yasuhiko Kijima, Akira Ito, Kenji Ishii
  • Patent number: 4841097
    Abstract: 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: Grant
    Filed: April 13, 1988
    Date of Patent: June 20, 1989
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hitoshi Takita, Fumihiko Kimura, Sakuo Noda, Yutaka Mukaida, Toyohiko Nitta, Hidetoshi Kobayashi
  • Patent number: 4751307
    Abstract: Disclosed are improved Wittig reaction processes wherein the Wittig reaction is conducted in an anisole containing solvent.
    Type: Grant
    Filed: February 27, 1987
    Date of Patent: June 14, 1988
    Assignee: Mallinckrodt, Inc.
    Inventor: Carl R. White
  • Patent number: 4723036
    Abstract: 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: Grant
    Filed: September 30, 1982
    Date of Patent: February 2, 1988
    Assignee: Kuraray Company, Ltd.
    Inventors: Takanori Kitamura, Masuhiko Tamura
  • Patent number: 4618704
    Abstract: 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: Grant
    Filed: April 3, 1979
    Date of Patent: October 21, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Martin Weitz, Rolf Fischer
  • Patent number: 4593115
    Abstract: 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: Grant
    Filed: November 21, 1984
    Date of Patent: June 3, 1986
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akio Miyake, Masayoshi Yamaoka
  • Patent number: 4568782
    Abstract: 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: Grant
    Filed: June 17, 1985
    Date of Patent: February 4, 1986
    Assignee: The Standard Oil Company
    Inventors: Marco Pagnotta, Mark C. Cesa, James D. Burrington
  • Patent number: 4520125
    Abstract: 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: Grant
    Filed: February 23, 1984
    Date of Patent: May 28, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl Baer, Peter Bassler, Gerd Duembgen, Gerd Fouquet, Richard Krabetz, Franz Merger, Friedbert Nees
  • Patent number: 4518797
    Abstract: 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: Grant
    Filed: March 15, 1979
    Date of Patent: May 21, 1985
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4518796
    Abstract: 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: Grant
    Filed: May 13, 1980
    Date of Patent: May 21, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Atsushi Aoshima, Yoshio Suzuki, Setsuo Yamamatsu, Tatsuo Yamaguchi
  • Patent number: 4493801
    Abstract: 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: Grant
    Filed: November 2, 1981
    Date of Patent: January 15, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Gerhard Nestler
  • Patent number: 4440946
    Abstract: 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: Grant
    Filed: July 26, 1982
    Date of Patent: April 3, 1984
    Assignee: Celanese Corporation
    Inventors: Richard H. Summerville, deceased, James E. Summerville, Jr., administrator
  • Patent number: 4399302
    Abstract: 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: Grant
    Filed: February 25, 1982
    Date of Patent: August 16, 1983
    Assignee: Degussa Aktiengesellschaft
    Inventors: Kleemann, Axel, Rudolf Fahnenstich, Marc Samson
  • Patent number: 4380663
    Abstract: 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: Grant
    Filed: October 20, 1977
    Date of Patent: April 19, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Roscher, Helmut Schaum, Heinz Schmitz
  • Patent number: 4353832
    Abstract: 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: Grant
    Filed: June 5, 1980
    Date of Patent: October 12, 1982
    Assignee: INTEROX (Societe Anonyme)
    Inventors: Andre Lecloux, Claude Declerck, Franz Legrand
  • Patent number: 4322355
    Abstract: 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: Grant
    Filed: April 15, 1980
    Date of Patent: March 30, 1982
    Assignee: National Distillers & Chemical Corp.
    Inventors: David Horvitz, William D. Baugh
  • Patent number: 4314072
    Abstract: 2-(2-Hydroxy-3-oxobutyl)-3,3-dimethylcyclopropanecarbaldehyde and certain derivatives thereof are useful intermediates for the preparation of dihalovinyl-type pyrethroid esters.
    Type: Grant
    Filed: November 23, 1979
    Date of Patent: February 2, 1982
    Assignee: Shell Oil Company
    Inventor: Johannes L. M. Syrier
  • Patent number: 4301084
    Abstract: 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: Grant
    Filed: August 31, 1979
    Date of Patent: November 17, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Harald Laas, Axel Nissen, Bernd Meissner
  • Patent number: 4298757
    Abstract: 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: Grant
    Filed: July 9, 1979
    Date of Patent: November 3, 1981
    Assignee: Shell Oil Company
    Inventors: Johannes Van Berkel, Hendrik C. Kelderman
  • Patent number: 4277633
    Abstract: 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: Grant
    Filed: July 12, 1979
    Date of Patent: July 7, 1981
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Satoru Enomoto, Hisayuki Wada, Sadao Nishita, Yutaka Mukaida, Mikiro Yanaka, Hitoshi Takita
  • Patent number: 4273934
    Abstract: 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: Grant
    Filed: April 17, 1979
    Date of Patent: June 16, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Hans-Juergen Foerster
  • Patent number: 4263443
    Abstract: 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: Grant
    Filed: November 22, 1978
    Date of Patent: April 21, 1981
    Assignee: Halcon Research and Development Corp.
    Inventor: John F. White
  • Patent number: 4258207
    Abstract: 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: Grant
    Filed: March 15, 1979
    Date of Patent: March 24, 1981
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4258205
    Abstract: 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: Grant
    Filed: December 4, 1978
    Date of Patent: March 24, 1981
    Assignee: Shell Oil Company
    Inventors: Johannes Van Berkel, Hendrik C. Kelderman
  • Patent number: 4254280
    Abstract: 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: Grant
    Filed: November 23, 1979
    Date of Patent: March 3, 1981
    Assignee: Shell Oil Company
    Inventor: Johannes Syrier
  • Patent number: 4249019
    Abstract: 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: Grant
    Filed: November 13, 1978
    Date of Patent: February 3, 1981
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Nobuhiro Tamura, Yohei Fukuoka, Setsuo Yamamatsu, Yoshio Suzuki, Ryoichi Mitsui, Tadayuki Ibuki
  • Patent number: 4229592
    Abstract: 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: Grant
    Filed: February 6, 1978
    Date of Patent: October 21, 1980
    Assignee: Kansas University Endowment Association
    Inventors: Lester A. Mitscher, George W. Clark, III, Paul B. Hudson
  • Patent number: 4225726
    Abstract: 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: Grant
    Filed: May 23, 1979
    Date of Patent: September 30, 1980
    Assignee: Eastman Kodak Company
    Inventors: Don L. Morris, Anthony W. McCollum
  • Patent number: 4214099
    Abstract: 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: Grant
    Filed: June 22, 1978
    Date of Patent: July 22, 1980
    Assignee: Pfizer Inc.
    Inventors: Elias J. Corey, Jasjit S. Bindra, Thomas K. Schaaf
  • Patent number: 4175204
    Abstract: 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: Grant
    Filed: January 8, 1979
    Date of Patent: November 20, 1979
    Inventor: James H. Babler
  • Patent number: 4133836
    Abstract: 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: Grant
    Filed: May 31, 1977
    Date of Patent: January 9, 1979
    Assignee: BASF Aktiengesellschaft
    Inventors: Axel Nissen, Gerd Kaibel
  • Patent number: 4124619
    Abstract: 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: Grant
    Filed: March 23, 1977
    Date of Patent: November 7, 1978
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Peter Fitton, Harold Moffet
  • Patent number: 4118406
    Abstract: 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: Grant
    Filed: August 8, 1977
    Date of Patent: October 3, 1978
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Jurgen Bestmann, Werner Theo Stransky, Otto Vostrowsky
  • Patent number: 4100110
    Abstract: 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: Grant
    Filed: August 11, 1975
    Date of Patent: July 11, 1978
    Assignee: Bush Boake Allen Limited
    Inventors: Hifzur Rahman Ansari, Neville Unwin, Horst Richard Wagner
  • Patent number: 4087435
    Abstract: 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: Grant
    Filed: February 17, 1977
    Date of Patent: May 2, 1978
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., James H. Jones, John B. Bicking
  • Patent number: 4072709
    Abstract: 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: Grant
    Filed: May 27, 1975
    Date of Patent: February 7, 1978
    Assignee: Monsanto Company
    Inventor: Harold B. Tinker
  • Patent number: 4069258
    Abstract: 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: Grant
    Filed: March 15, 1976
    Date of Patent: January 17, 1978
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Hoffmann, Karl VON Fraunberg
  • Patent number: 4069385
    Abstract: 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: Grant
    Filed: June 3, 1976
    Date of Patent: January 17, 1978
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masashi Araki, Tsuneyuki Nagase
  • Patent number: 4049682
    Abstract: 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: Grant
    Filed: September 15, 1976
    Date of Patent: September 20, 1977
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan Owen Pittet, Erich Manfred Klaiber, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals
  • Patent number: 4048195
    Abstract: 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: Grant
    Filed: July 14, 1976
    Date of Patent: September 13, 1977
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Zoltan George Hajos