Acyclic Carbon To Carbon Unsaturation Containing Patents (Class 568/813)
  • Patent number: 5347056
    Abstract: This invention relates to a process for producing .alpha., .beta.-unsaturated alcohol, which uses unsaturated aldehyde as a starting material, and in which only the aldehyde group in the unsaturated aldehyde is selectively hydrogenated by hydrogen transfer reaction, while the carbon-carbon double bond is left as it is. The method is characterized by using a catalyst which contains at least one oxide selected from the group consisting of oxides of yttrium, lanthanum, praseodymium, neodymium and samarium, as a main active ingredient. The catalysts exhibit high activity and selectivity, as well as a long life span.
    Type: Grant
    Filed: August 4, 1993
    Date of Patent: September 13, 1994
    Assignee: Mitsubishi Petrochemical Company, Ltd.
    Inventors: Yoshihisa Watanabe, Mitsuhiko Kurashige
  • Patent number: 5334776
    Abstract: A compound represented by the general formula (I) and a separating agent comprising the same: ##STR1## wherein Ar and Ar' are each an aromatic group; and the positional relationship of the two substituents on the central benzene ring may be any of ortho, meta and para.The above compound is effective in the separation and purification of many compounds and enables the provision of various compounds (such as intermediates of drugs) which are useful in the field of fine chemicals, particularly optically active substances, at high purities and in large amounts.
    Type: Grant
    Filed: March 12, 1993
    Date of Patent: August 2, 1994
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Fumio Toda
  • Patent number: 5258529
    Abstract: The present invention provides a process for producing a propargylcarbinol compound of formula (I): ##STR1## where R.sup.1 and R.sup.2 are as defined herein. The process comprises reacting a haloallycarbinol compound of formula (II) with a base. The present invention also relates to a process for producing the haloallylcarbinol compound. The above propargylcarbinol compound is useful as an intermediate for agrochemicals, pharmaceuticals, perfumes, resin monomers, and the like.
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: November 2, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiaki Oda, Sanshiro Matsuo, Kenji Saito
  • Patent number: 5248834
    Abstract: Pesticidal compounds of formula II: R.sub.A CR.sub.3 .dbd.CR.sub.4 CHDR.sub.Bin which formula:R.sub.A represents a group ArCR.sub.1 R.sub.2 - in which Ar represents a phenyl or naphthyl group optionally substituted by one or more halogen, alkoxy, haloalkoxy, methylenedioxy, C.sub.1 -C.sub.6 alkyl or haloalkyl groups;R.sub.1 and R.sub.2 together with the carbon to which they are attached represent a C.sub.3 -C.sub.6 cycloalkyl group optionally substituted by one or more halogen atoms or C.sub.1 -C.sub.6 alkyl groups.R.sub.3 and R.sub.4 which may be identical or differ, represent hydrogen halogen or C.sub.1 -C.sub.6 alkyl groups andR.sub.B represents the residue of an alcohol R.sub.B CHDOH in which D is hydrogen or cyano and of which the [1R, cis] 2,2-dimethyl-3-(2,2-dibromovinyl) cyclopropane carboxylic ester is significantly insecticidal,the configuration of R.sub.A and CHDR.sub.
    Type: Grant
    Filed: April 17, 1992
    Date of Patent: September 28, 1993
    Assignee: British Technology Group Limited
    Inventors: Michael Elliott, Norman F. Janes, Bhupinder P. S. Khambay, Ahmet Baydar
  • Patent number: 5210332
    Abstract: An iridium-optically active phosphine complex represented by formula (I):[H.sub.2 Ir(L.sup.1)(L.sup.2)]Y (I)wherein L.sup.1 represents an optically active phosphine compound represented by formula (II): ##STR1## wherein Ar represents a phenyl group or a p- and/or m-lower alkyl-substituted phenyl group, or formula (III): ##STR2## L.sup.2 represents a tertiary phosphine compound represented by formula (IV): ##STR3## wherein Z represents a lower alkoxy group or a di-lower alkylamino group; and A represents an integer of from 1 to 3; Y represents BF.sub.4, PF.sub.6, ClO.sub.4, or BPh.sub.4, wherein Ph represents a phenyl group,and a process for producing an optically active alcohol using the above complex as an enantioselective catalyst are disclosed. The complex exhibits excellent catalytic activity to give high enantioselective yields in enantioselective synthesis, particularly enantioselective hydrogenation.
    Type: Grant
    Filed: March 20, 1992
    Date of Patent: May 11, 1993
    Assignee: Takasago International Corporation
    Inventors: Takanao Taketomi, Susumu Akutagawa, Hidenori Kumobayashi, Hidemasa Takaya, Kazushi Mashima
  • Patent number: 5202502
    Abstract: A chemically and optically pure B-halodiiso-2-ethylapopinocampheylborane of essentially 100% ee represented by the formula: ##STR1## wherein B is borane and X is halo, and a process of using such for the production of optically active alcohols.
    Type: Grant
    Filed: March 23, 1992
    Date of Patent: April 13, 1993
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5157167
    Abstract: The novel organoboron reagent of the present invention is useful in the preparation of unsubstituted propargylic alcohols. This compound reacts with aldehydes and ketones cleanly to afford propargylic alcohols in excellent yields Unsubstituted propargylic alcohols are important synthetic intermediates in the synthesis of a number of natural products. In addition, the novel organoboron reagent of the present invention also demonstrates diastereomeric selectivity when reacted with enatiomerically pure aldehydes.
    Type: Grant
    Filed: January 31, 1992
    Date of Patent: October 20, 1992
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Jonathan C. Evans, Christian T. Goralski
  • Patent number: 5136083
    Abstract: The present invention relates to a process for the purification of 4-acetoxystyrene from a crude product mixture comprising 4-acetoxystyrene and typically 5 or more contaminants in substantial amount.The crude product mixture is purified by melt crystallization by cooling the mixture to a temperature ranging from about +8.degree. C. to about -50.degree. C., whereby at least a first portion of the mixture is crystallized; removing the liquid remaining from contact with the crystallized first portion of the mixture; and, subsequently slowly heating the crystallized first portion, while simultaneously removing liquid which forms due to the heating, whereby impurities contained in the liquid which forms are removed from the crystallized first portion.Surprisingly, despite the large number of contaminants present, and use of the process to purify crude product mixtures containing as little as 50% by weight 4-acetoxystyrene, purities as high as 99.
    Type: Grant
    Filed: August 30, 1990
    Date of Patent: August 4, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Jack Chosnek, George E. Beck, Donna L. Keene, Siegbert Rittner, Volker Hautzel
  • Patent number: 5116981
    Abstract: This invention encompasses novel analogs of Leukotriene B.sub.4 which are selected from a compound of formula I, B--C.apprxeq.C--CH.sub.2 C(M.sub.2)--C.apprxeq.C--Y--C(M.sub.1)--A, or formula II, B--C.apprxeq.C--CH.sub.2 C(M.sub.2)--C.apprxeq.C--P--R.sub.5 --A: wherein Y is: ##STR1## wherein P is: ##STR2## Patentable intermediates, process for making the novel analogs and intermediates and preparation of useful pharmacological agents comprising the analogs and intermediates are part of this invention.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: May 26, 1992
    Assignee: The Upjohn Company
    Inventor: Joel Morris
  • Patent number: 5091598
    Abstract: Process of preparation of alcohols by the reaction of an organic halide with a carbonyl compound in an organic solvent, in the presence of metallic manganese, followed by hydrolysis of the reaction product; the reaction is initiated and activated by an ester present in the reaction medium.
    Type: Grant
    Filed: December 28, 1988
    Date of Patent: February 25, 1992
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Gerard Cahiez, Pierre-Yves Chavant, Pierre Tozzolino
  • Patent number: 5068368
    Abstract: A process for the preparation of ethynyl carbinols of the formula: ##STR1## wherein R" is hydrogen, a substituted or unsubstituted aliphatic or aromatic hydrocarbon, R'" is a substituted or unsubstituted aliphatic or aromatic hydrocarbon or R" and R'" together to the carbon atom to which they are joined represent a steroid, which comprises the steps ofA. reacting in a solvent system comprising an aromatic hydrocarbon, at least one lithium alkylamide selected from the group consisting of: ##STR2## wherein R is a hydrogen or lower alkyl, R' is hydrogen, lower alkyl, a substituted or unsubstituted aliphatic, alicyclic or aromatic hydrocarbon, x is an integer of 2 to 8, y and z are each 0 to 1, with acetylene to form a monolithium acetylideB. reacting in a solvent system comprising an aromatic hydrocarbon, the monolithium acetylene from Part A with a ketone of the formula R"R'"C.dbd.O, wherein R" and R'" are as hereinbefore defined, and thenC.
    Type: Grant
    Filed: May 10, 1990
    Date of Patent: November 26, 1991
    Assignee: Cyprus Foote Mineral Company
    Inventors: W. Novis Smith, Christopher Louer
  • Patent number: 5017583
    Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are leukotriene antagonists. These compounds inhibit SRS-A and leukotriene synthesis and are antagonists of SRS-A and are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.
    Type: Grant
    Filed: February 23, 1988
    Date of Patent: May 21, 1991
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Joshua Rokach, Haydn R. Williams, Masatoshi Kakushima, Yvan Guindon
  • Patent number: 5004843
    Abstract: Process for preparing predominantly Z-substituted allylic alcohols of the formula: ##STR1## wherein R.sup.1 is a straight or branched C.sub.1 -C.sub.25 alkyl group optionally bearing at least one substituent and/or at least one unsaturated linkage and R.sup.2 is a hydrogen atom or a methyl group, which comprises reacting a vinyl epoxide of the formula: ##STR2## wherein R.sup.2 is as defined above with an organolithium compound of the formula above. More particularly, there is disclosed a process for R.sup.1 --Li wherein R.sup.1 is as defined above; particularly, process for preparing .alpha.-santalol of the formula: ##STR3## which comprises reacting 3-methyl-3,4-epoxybutene-1 with lithiomethyl-2,3-dimethyltricyclo[2.2.1.0.sup.2,6 ]heptane.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: April 2, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsuhisa Tamura, Gohu Suzukamo, Ken-ichi Hirose
  • Patent number: 4978794
    Abstract: 2-Alkenylbis(2-isocaranyl)boranes represented by the formula: ##STR1## wherein R is 2-alkenyl. The compounds undergo asymmetric 2-alkenylboration with a variety of aldehydes and afford the corresponding alcohols in 94-99% ee.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: December 18, 1990
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4973768
    Abstract: Unsaturated alcohols are prepared by hydrogenation of the corresponding carbonyl compounds in the presence of a platinum-cobalt bi-metallic catalyst having an alloy structure.
    Type: Grant
    Filed: March 6, 1989
    Date of Patent: November 27, 1990
    Assignee: Rhone-Poulenc Sante
    Inventors: Georges Cordier, Pierre Fouilloux, Jean-Michel Grosselin
  • Patent number: 4958033
    Abstract: A process for preparing an alcohol of the formula: ##STR1## by reacting a carbonyl compound of the formula: ##STR2## or an oxirane of the formula: ##STR3## magnesium and a propargyl halide of the formula: ##STR4## followed by hydrolysis, characterized in that the carbonyl compound (II) or the oxirane compound (III) and the propargyl halide (IV) are reacted simultaneously with magnesium in an inert solvent in the presence of zinc or a halide thereof.
    Type: Grant
    Filed: September 26, 1986
    Date of Patent: September 18, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukihisa Takisawa, Nobuharu Kono, Kenji Saito, Hiroshi Yamachika
  • Patent number: 4956502
    Abstract: A process for preparing a compound of the formula ##STR1## in which both Rs and H or OH; comprising the steps a. of treating the ethyl ester of caffeic acid with trialkylsilyl chloride at ambient conditions in equimolar proportions in the presence of a base;b. the reduction of the ester to the corresponding allylic alcohol with aluminum hydride reagent;c. of oxidizing the resulting product with manganese dioxide at ambient temperature and in excess molar proportion to yield the corresponding allylic aldehyde;d. of coupling the latter with the silyl ether of the relative phenyl acetylide; ande. of hydrolysis of this coupled product with alkylammonium fluoride at ambient conditions in equimolar proportions.
    Type: Grant
    Filed: June 13, 1989
    Date of Patent: September 11, 1990
    Assignee: Rooperol (N.A.) NV
    Inventors: George L. Wenteler, Karl H. Regel, Siegfried Drews, Hans Kundig
  • Patent number: 4950796
    Abstract: Novel benzonitriles, benzaldehydes and benzyl alcohols of the formula I ##STR1## where R.sup.1 is methyl or ethyl, R.sup.2 is alkyl, alkenyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, or C.sub.1 -C.sub.5 -alkyl-substituted cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl, X is hydrogen, chlorine or fluorine and Z is --CN, CHO or ##STR2## where R.sup.3 is hydrogen, cyano, C.sub.2 -C.sub.4 -alkynyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.1 -C.sub.4 -alkyl, with the proviso that R.sup.2 is not --CH.sub.2 --CH.dbd.CH--B when B is hydrogen, alkyl or alkenyl and at the same time R.sup.1 is methyl and Z is ##STR3## and with the proviso that R.sup.2 is not methyl or ethyl when R.sup.1 is methyl and at the same time Z is ##STR4## and furthermore with the proviso that R.sup.2 is not methyl when R.sup.1 is methyl or ethyl and at the same time Z is --CN or --CHO.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: August 21, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Wolf, Hans Theobald, Norbert Goetz
  • Patent number: 4933511
    Abstract: An enantioselective process for the preparation of homoallyl alcohol enantiomer of formula II ##STR1## wherein: X.sup.1, X.sup.2 and X.sup.3 independently chosen from the group consisting of hydrogen, chlorine, bromine, fluorine, iodine, C.sub.1 to C.sub.6 alkyl, C.sub.1 and C.sub.6 haloalkyl, and haloaryl; andR.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently chosen from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, benzyl, substituted benzyl, phenyl, substituted phenyl; or R.sup.3 and R.sup.4 is as hereinbefore defined and R.sup.1 and R.sup.2 form a carbocyclic or heterocyclic ring; which process comprises; reacting an aldehyde of formula III with an alkene or formula IV in the presence of an optically-active organometallic catalyst. ##STR2## Furthermore, the compound of formula II can be isomerized to the allylic alcohol of formula I with retention of optical purity.
    Type: Grant
    Filed: April 7, 1987
    Date of Patent: June 12, 1990
    Assignee: ICI Australia Limited
    Inventors: Matthew Gredley, Colin Wilshire
  • Patent number: 4931589
    Abstract: A compound of formula (I) ##STR1## its isomers and its salts in which R.sub.1, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, halogen, C.sub.1 -C.sub.8 acyloxy or hydroxyl;R' is hydrogen or C.sub.1 -C.sub.6 -alkyl;R" is either a polyene chain or a benzene ring are useful in cosmetics and in the treatment of various dermatological and other complaints.
    Type: Grant
    Filed: July 13, 1988
    Date of Patent: June 5, 1990
    Assignee: L'Oreal
    Inventors: Gerard Lang, Jean Maignan, Serge Restle, Braham Shroot
  • Patent number: 4929776
    Abstract: Unsaturated alcohols are prepared by hydrogenation of the corresponding unsaturated carbonyl compounds in a homogeneous medium and in the presence of a ruthenium-based catalyst.
    Type: Grant
    Filed: November 29, 1988
    Date of Patent: May 29, 1990
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Michel Grosselin, Claude Mercier
  • Patent number: 4925990
    Abstract: Unsaturated alcohols are prepared by the hydrogenation of an unsaturated carbonyl compound in a two-phase liquid medium and in the presence of a catalyst consisting of a ruthenium derivative associated with a water-soluble ligand or a complex of ruthenium with a water-soluble ligand.
    Type: Grant
    Filed: November 29, 1988
    Date of Patent: May 15, 1990
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Michel Grosselin, Claude Mercier
  • Patent number: 4912253
    Abstract: An efficient method is proposed for the synthesis of an unsaturated alcohol of the general formula R--CH.dbd.CH(CH.sub.2).sub.n+1 OH, in which R is a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms and the subscript n is an integer in the range from 3 to 10, in which an acetate of the formula R--CH.dbd.CHCH.sub.2 OCOCH.sub.3 is subjected to a coupling reaction with a Grignard reagent of the formula X.sup.1 Mg(CH.sub.2).sub.n OMgX.sup.2, in which X.sup.1 and X.sup.2 are each a halogen atom, and then the reaction product is hydrolyzed. When the reaction product of the coupling reaction is reacted with acetic anhydride instead of hydrolysis, the corresponding acetate can readily be obtained. These unsaturated alcohols and acetates form a class of important biologically active compounds or intermediates thereof including sex pheromone compounds of insects.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: March 27, 1990
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takehiko Fukumoto, Akira Yamamoto
  • Patent number: 4892940
    Abstract: An aromatic naphthyl compound of the formula ##STR1## wherein n is 0 or 1,R' is hydrogen, OH, acyloxy, alkoxy or NH.sub.2,R" is hydrogen or lower alkoxy, or R' and R" taken together form an oxo, methano or hydroxy-imino radical,R is --CH.sub.2 OH or --COR.sub.8,R.sub.8 is hydrogen, --OR.sub.9 or ##STR2## R.sub.9 is hydrogen, alkyl having 1-20 carbon atoms, mono or polyhydroxyalkyl, aryl, aralkyl, the residue of a sugar or ##STR3##is 1, 2 or 3,r' and r" each independently represent hydrogen, alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl, benzyl, the residue of amino acid or the residue of aminated sugar, or r' and r" together form a heterocycle,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represent hydrogen, lower alkyl, alkoxy having 1-4 carbon atoms, fluoroalkoxy, CF.sub.3, cycloalkyl, lower acyl, halogen, OH, amino, acylamino or alkoxy carbonyl,R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or methyl or when n=1, R.sub.5 and R.sub.
    Type: Grant
    Filed: May 22, 1987
    Date of Patent: January 9, 1990
    Assignee: L'Oreal
    Inventors: Jean Maignan, Gerard Lang, Gerard Malle, Serge Restle, Braham Shroot
  • Patent number: 4871868
    Abstract: A method of producing substituted acetylenic compounds which comprises: reacting an organic compound having the general formula ofA--X (I)wherein A represents a saturated or unsaturated aliphatic hydrocarbon residue of 1-20 carbon atoms which may have one or more substituents inactive in the reaction, and X represents a halogen atom or an arylsulfonyloxy group, with a metal acetylide having the general formula ofM--C.tbd.C--B (II)wherein M represents an alkali metal, and B represents (a) a hydrogen, (b) a saturated or unsaturated hydrocarbon residue which may have one or more substituents inactive in the reaction, or (c) a saturated or unsaturated hydrocarbon residue which has a substituent having the general formula of--C.tbd.C--M (III)wherein M represents an alkali metal, in the presence of an alkyl-2-imidazolidinone having the general formula of ##STR1## wherein R.sup.1 and R.sup.2 independently represent a lower alkyl, and R.sup.3 represents a hydrogen or a lower alkyl.
    Type: Grant
    Filed: March 3, 1988
    Date of Patent: October 3, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yuzuru Saito, Kokichi Yoshida
  • Patent number: 4853414
    Abstract: Compounds of formula (I), useful as insecticides and knockdown agents: ##STR1## where Y is C.sub.1-6 alkoxy, Z is halo or C.sub.1-6 alkoxy; R is --(CH.sub.2).sub.p --(O).sub.m --R.sup.3 where m and p may be 0 or 1; R.sup.3 is C.sub.1-6 alkyl, phenyl or benzyl, or when m is 0, R.sup.3 is C.sub.1-6 alkenyl, haloalkenyl, alkynyl or haloalkynyl, and either (a) A and B are both C.sub.1-4 alkyl or (b) A is hydrogen and B is (R.sup.1)(R.sup.2)C.dbd.CH-- where R.sup.1 and R.sup.2 are selected from methyl, chloro, bromo, fluoro and trifluoromethyl.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: August 1, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Robson, John Williams
  • Patent number: 4825012
    Abstract: Allylic 1-hydroxy alcohols are inverted to allylic 3-hydroxy alcohols by: (1) epoxidizing the allyl group of the allylic 1-hydroxy alcohol to the corresponding 2,3-epoxy-1-hydroxy alcohol; (2) transforming the 2,3-epoxy-1-hydroxy alcohol compound to a 1,2-dihalo-3-hydroxy alcohol; and (3) dehalogenating the 1,2-dihalo-3-hydroxy alcohol to form the desired allylic 3-hydroxy alcohol.
    Type: Grant
    Filed: December 7, 1987
    Date of Patent: April 25, 1989
    Assignee: Akzo America Inc.
    Inventor: Andrea Leone-Bay
  • Patent number: 4783549
    Abstract: A compound of formula (I) ##STR1## its isomers and its salts in which --R.sub.1, R.sub.3 and R.sub.4 are each indepenently hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, halogen, C.sub.1 -C.sub.8 -acyloxy or hydroxyl;--R' is hydrogen or C.sub.1 -C.sub.6 -alkyl;--R" is either a polyene chain or a benzene ring are useful in cosmetics and in the treatment of various dermatological and other complaints.
    Type: Grant
    Filed: September 4, 1985
    Date of Patent: November 8, 1988
    Assignee: L'Oreal
    Inventors: Gerard Lang, Jean Maignan, Serge Restle, Braham Shroot
  • Patent number: 4782188
    Abstract: The invention is a process for the hydroformylation of C.sub.2-4 alkenes, formyl-substituted C.sub.2-4 alkenes, aryl-substituted alkenes, unsaturated norbornane ring-containing compounds, and .alpha.-unsaturated acetals which comprises contacting a C.sub.2-4 alkene, a formyl-substituted C.sub.2-4 alkene, aryl-substituted alkene, an unsaturated norbornane ring-containing compound or an .alpha.-unsaturated acetal in a polar organic solvent with water and carbon monoxide in the presence of a catalytic amount of a catalyst which comprises a mixture of (a) an alkali metal iron carbonyl or alkaline earth metal iron carbonyl which corresponds to the formula M.sub.a Fe.sub.x (CO).sub.y and (b) iron pentacarbonyl under conditions such that an alcohol or aldehyde derivative of a C.sub.2-4 alkene, a formyl-substituted C.sub.2-4 alkene, an aryl-substituted alkene, unsaturated norbornane ring-containing compound or an .alpha.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: November 1, 1988
    Assignee: The Dow Chemical Company
    Inventor: Susan B. Butts
  • Patent number: 4756840
    Abstract: Described is the novel compound genus, the beta-alkylidene phenethyl alcohols of our invention, defined according to the generic structure: ##STR1## (wherein R.sub.1 represents hydrogen or methyl, useful in augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener articles, fabric softener compositions, cosmetic powders and hair preparations).
    Type: Grant
    Filed: September 3, 1987
    Date of Patent: July 12, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko
  • Patent number: 4731488
    Abstract: A catalyst for vapor-phase hydrogen transfer reaction between a carbonyl compound having an alkenyl or aryl group and a primary or secondary alcohol, said catalyst having a composition represented by the following general formulaMg.sub.a X.sub.b Y.sub.c O.sub.dwherein X represents at least one element selected from the group consisting of boron, aluminum, silicon, phosphorus, titanium, vanadium, iron, yttrium, zirconium, niobium, tin, antimony, lead, bismuth, lanthanum and cerium, Y represents at least one element selected from the group consisting of alkali metals and alkaline earth metals excepting magnesium, O represents oxygen, and a, b, c and d represent the atomic ratios of the individual elements, and when a is 1, b represents a number of 0.01 to 0.5, c represents a number of 0 to 0.5, and d is a number determined by the atomic valences and atomic ratios of the individual elements.
    Type: Grant
    Filed: June 6, 1986
    Date of Patent: March 15, 1988
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Yuuji Shimasaki, Youichi Hino, Michio Ueshima
  • Patent number: 4663478
    Abstract: By reacting a phenol compound with an organic halide selected from the group consisting of a haloform, a carbon tetrahalide and a substituted or unsubstituted allyl halide in the presence of an alkali metal hydroxide, using as a catalyst a fixed cyclodextrin having hydroxyl groups crosslinked with a bivalent hydrocarbon group having free valences at its both ends, said hydrocarbon group having at least one hydrogen atom substituted or unsubstituted with a member selected from the group consisting of an alkyl group, a halogen atom and a hydroxyl group and containing or not containing at least one combination of two neighboring carbon atoms having therebetween at least one member selected from the group consisting of an oxygen atom, a sulfur atom and a phenylene, various useful para-substituted phenol derivatives can be advantageously obtained.
    Type: Grant
    Filed: April 18, 1985
    Date of Patent: May 5, 1987
    Assignee: Hidefuni Hirai
    Inventors: Hidefuni Hirai, Makoto Komiyama, Izuru Sugiura
  • Patent number: 4644085
    Abstract: The invention relates to a new anti-cancer chemical compound which has been called rooperol and certain derivatives thereof of the general formula ##STR1## in which A is chosen from the group including a phenyl group, a substituted phenyl group and --CH.sub.2 --O--R.sup.5 where R.sup.5 =H, an alkyl (C.sub.1 -C.sub.5), aralkyl or acyl substituent; R.sup.1 and R.sup.2 are chosen from substituents including H for both or singly if one of them is --OH, --NH.sub.2, --SH, ##STR2## or taken together R.sup.1 and R.sup.2 are =0; R.sup.3 is H or ##STR3## where R.sup.6 is an alkyl group (C.sub.1 -C.sub.7); either of R.sup.4 or B are chosen from substituents including H, ##STR4## a phenyl group, substituted phenyl group or a furyl group.
    Type: Grant
    Filed: June 4, 1985
    Date of Patent: February 17, 1987
    Assignee: Rooperol (NA) NV
    Inventors: Siegfried Drewes, Roelof W. Liebenberg
  • Patent number: 4620045
    Abstract: Eneynols are prepared from terminal acetylenes and propargylic alcohols using a Cu.sup.+, Ag.sup.+ and/or Au.sup.+ halide catalyst.
    Type: Grant
    Filed: March 19, 1985
    Date of Patent: October 28, 1986
    Assignee: The Dow Chemical Company
    Inventors: Giffin D. Jones, Harold E. Doorenbos
  • Patent number: 4564476
    Abstract: Aryl fatty acid compounds of the formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, X, and Y are as defined herein are novel and useful in the treatment of allergic and inflammatory disorders.
    Type: Grant
    Filed: October 29, 1984
    Date of Patent: January 14, 1986
    Assignee: McNeilab, Inc.
    Inventor: Chih Y. Ho
  • Patent number: 4560786
    Abstract: .DELTA..sup.8,9 -Prostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 ; A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH;B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--W is a free or functionally modified hydroxymethylene group or free or functionally modified ##STR4## wherein the OH--group can be in the .alpha.-- or .beta.-- position; D and E jointly are a direct bond orD is straight chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen, sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine or alkyl;R.sub.4 is free or functionally modified hydroxy andR.sub.
    Type: Grant
    Filed: June 24, 1982
    Date of Patent: December 24, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
  • Patent number: 4549029
    Abstract: Novel substituted tetrahydrofurans having a six-membered ring in the 4 position and methyl substituents in the 2 and 4 positions possess organoleptic properties described as fruity, citrus-like and reminiscent of grapefruit. These compounds are useful in fragrances and flavors.
    Type: Grant
    Filed: April 5, 1983
    Date of Patent: October 22, 1985
    Assignee: Givaudan Corporation
    Inventor: Alan R. Hochstetler
  • Patent number: 4536347
    Abstract: Ruthenium-on-charcoal and ruthenium-on-carbon black catalysts, containing from 0.1 to 5% by weight of iron, for the preparation of olefinically unsaturated alcohols by selective hydrogenation of the corresponding .alpha., .beta.-unsaturated carbonyl compounds in the liquid phase are prepared by modifying the catalyst with iron only after it has been impregnated with the ruthenium compound, and reducing the catalyst with hydrogen at from 400.degree. to 600.degree. C., with thorough mixing.The catalysts according to the invention are particularly useful for improving the industrially difficult hydrogenation of citral to give the soughtafter fragrances geraniol and nerol.
    Type: Grant
    Filed: March 19, 1984
    Date of Patent: August 20, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Horner, Matthias Irgang
  • Patent number: 4526993
    Abstract: Conjugated dienols for providing cure sites to air-drying acrylic finishes are prepared from conjugated dienoic acids by conversion to an activated ester followed by sodium borohydride reduction thereof.
    Type: Grant
    Filed: April 30, 1982
    Date of Patent: July 2, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Chaucer C. Tang
  • Patent number: 4523031
    Abstract: By reacting, using as a catalyst a modified or unmodified cyclodextrin, a phenol compound with an organic halide selected from the group consisting of a carbon tetrahalide and a substituted or unsubstituted allyl halide in the presence of an alkali metal hydroxide, a substituent group derived from said organic halide can be introduced to the para-position of the phenol compound with high selectivity, whereby various useful para-substituted phenol derivatives can be advantageously obtained.
    Type: Grant
    Filed: September 7, 1983
    Date of Patent: June 11, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Hidefumi Hirai, Makoto Komiyama
  • Patent number: 4523037
    Abstract: By reacting, using as a catalyst a modified or unmodified cyclodextrin, a phenol compound with a haloform in the presence of an alkali metal hydroxide, while maintaining the molar ratio of the cyclodextrin to the haloform at 0.5 to 10, a substituent group derived from the haloform can be introduced to the para-position of the phenol compound with high selectivity, whereby useful para-substituted phenol derivatives can be advantageously obtained.
    Type: Grant
    Filed: September 7, 1983
    Date of Patent: June 11, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Hidefumi Hirai, Makoto Komiyama
  • Patent number: 4469902
    Abstract: Novel 1-iodoprop-1-yn-3-ols of the formula ##STR1## in which R.sup.1 represents optionally substituted aryl andR.sup.2 represents alkyl or cycloalkyl, which may be used as plant protection agents, especially as fungicides, are obtained when 1-iodoprop-1-yn-3-ols are reacted with iodine in the presence of a basic compound.
    Type: Grant
    Filed: May 14, 1982
    Date of Patent: September 4, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Jager, Wilhelm Brandes, Paul-Ernst Frohberger
  • Patent number: 4467102
    Abstract: An optically active propargyl alcohol derivative of the formula (I) ##STR1## wherein X=phenyl or thienyl and R=lower alkyl, halogenated methyl, phenyl or substituted phenyl having at least one lower alkyl radical and or halogen atom, is prepared by contacting a racemic modification of l- and d-isomers of the formula (I) with l-brucine in an organic solvent, by separating the resultant deposited diastereomer from a solution containing the resultant other diastereomer in the organic solvent, by decomposing each diastereomer with an aqueous mineral acid solution in the presence of an organic solvent capable of dissolving the corresponding optically active isomer dissociated from the diastereomer and incompatible with water so as to allow the optically active isomer to be dissolved in the water-incompatible organic solvent, and by recovering the optically active isomer from the solution thereof.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: August 21, 1984
    Assignee: Ube Industries, Ltd.
    Inventors: Fumio Toda, Koichi Tanaka
  • Patent number: 4467118
    Abstract: There is disclosed a novel process for converting allylic amines, having a hydrogen bonded to a carbon .delta. to the amino group, to a diene in the presence of a zero valent palladium phosphine complex and a weak acid. The process has been used to make novel compositions containing 7-methoxy-3,7-dimethyloctadienes which are useful as odorants and flavorants.
    Type: Grant
    Filed: March 3, 1982
    Date of Patent: August 21, 1984
    Assignee: Givaudan Corporation
    Inventors: Alan J. Chalk, Steven A. Magennis, Vasile S. Wertheimer, Richard E. Naipawer
  • Patent number: 4455442
    Abstract: Olefinically unsaturated alcohols (I) are prepared by selective hydrogenation of the corresponding carbonyl compounds (II) in the liquid phase with hydrogen, using an Ru, Rh, Os, Ir or Pt catalyst and carrying out the hydrogenation in the presence of from 5 to 40% by weight, based on (II), of a tertiary amine.The process is of particular importance for the selective hydrogenation of .alpha.,.beta.-unsaturated carbonyl compounds (IIa) and amongst these specifically for the hydrogenation of citral to geraniol and nerol.The preferred amine is trimethylamine.
    Type: Grant
    Filed: July 8, 1980
    Date of Patent: June 19, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Horner, Matthias Irgang, Axel Nissen
  • Patent number: 4436939
    Abstract: A process for producing 1-(p-prenylphenyl)ethanol, which comprises reacting p-chloroprenylbenzene with magnesium at a temperature between 100.degree. C. and 150.degree. C. to form a Grignard reagent, and then reacting it with acetaldehyde.
    Type: Grant
    Filed: August 25, 1982
    Date of Patent: March 13, 1984
    Assignees: Taisho Pharmaceutical Co., Ltd., Kuraray Co., Ltd.
    Inventors: Takehiro Amano, Kensei Yoshikawa, Tatsuhiko Sano, Yutaka Ohuchi, Michihiro Ishiguro, Manzo Shiono, Yoshiji Fujita, Takashi Nishida
  • Patent number: 4320236
    Abstract: A process for the ethynylation of alpha, beta-unsaturated ketones to produce compounds containing the tertiary acetylenic alcohols which are useful as intermediates in carotenoids.
    Type: Grant
    Filed: September 19, 1980
    Date of Patent: March 16, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Hermann Wiederkehr
  • Patent number: 4288640
    Abstract: Process for carrying out exothermic reactions between a gas and a liquid in the presence of a solid catalyst by passing the gas and the liquid cocurrently through a packed reaction vessel, preferably of elongated shape, wherein the gas and liquid pass through the packed reaction vessel in transition flow.
    Type: Grant
    Filed: July 22, 1976
    Date of Patent: September 8, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Ludwig Schuster, Paul Raff, Herwig Hoffmann, Rolf Schneider, Erich Flickinger
  • 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: 4247718
    Abstract: An improved process for the preparation of .alpha.-.beta. unsaturated alcohols by the liquid phase catalytic hydrogenation of the corresponding aldehyde. An aldehyde is selected having the general formula ##STR1## wherein at least one of R.sub.1, R.sub.2 and R.sub.3 is an unsubstituted phenyl group or a phenyl group substituted with alkyl and/or alkoxy groups wherein the carbon atoms of the substituents on any phenyl group total no more than five, and the remainder of said R.sub.1, R.sub.2 and R.sub.3 independently represents hydrogen or an alkyl group having from 1 to 10 carbon atoms. The selected aldehyde is hydrogenated in the presence of a platinum catalyst in a liquid reaction medium of water and a water-immiscible organic solvent, wherein an alkali metal hydroxide and/or an alkali metal alkoxide promoter is dissolved in the water.
    Type: Grant
    Filed: March 13, 1979
    Date of Patent: January 27, 1981
    Assignee: Stamicarbon, B.V.
    Inventors: Jozef M. A. Dautzenberg, Joannes M. C. A. Mulders, Petrus A. M. J. Stijfs