Aldehyde Or Ketone Reactant Patents (Class 568/343)
  • Patent number: 5545761
    Abstract: A method of manufacturing 2,6,6-trimethyl-2-cyclohexen-1,4-dione (ketoisophorone) from 3,5,5-trimethyl-2-cyclohexenone (alpha-isophorone). The alpha-isophorone is reacted with hydroperoxide in a solvent, and in the presence of a metal catalyst. The reaction converts the alpha-isophorone directly to ketoisophorone without the intermediate isomerization of alpha-isophorone to beta-isophorone (3,5,5-trimethyl-3-cyclohexenone).
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: August 13, 1996
    Assignee: Aristech Chemical Corporation
    Inventors: Bryan T. Dawson, Joseph Pugach
  • Patent number: 5504255
    Abstract: The present invention provides special epoxy derivative (1), cyclohexanone derivative (2), cyclohexenone derivative (3) and 3-substituted cyclohexenone derivative (4) which are useful as intermediates for synthesizing physiologically active materials, and a method for stereoselectively introducing substituted groups. Further, the present invention provides a method for synthesizing optically active compounds, such as optically active carvone via these intermediates.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: April 2, 1996
    Assignee: Chisso Corporation
    Inventors: Seiichi Takano, Kunio Ogasawara
  • Patent number: 5453546
    Abstract: A process is described for the manufacture of .beta.-ionone by the sulphuric acid-catalyzed cyclization of pseudoionone in a two-phase solvent system comprising concentrated sulphuric acid and a second solvent essentially immiscible with water, which process comprises using carbon dioxide liquefied under pressure as the second solvent. This process is carried out, inter alia, under a pressure of about 50 bar to about 150 bar and at temperatures from about -15.degree. C. to about +15.degree. C. prior to the subsequent stopping (quenching) of the cyclization reaction. The process in accordance with the invention is preferably carried out continuously and is an important intermediate stage in the synthesis of vitamin A.
    Type: Grant
    Filed: June 2, 1994
    Date of Patent: September 26, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kurt Steiner, Herwig Ertel, Helmut Tiltscher
  • Patent number: 5446175
    Abstract: The present invention provides special epoxy derivative (1), cyclohexanone derivative (2), cyclohexenone derivative (3) and 3-substituted cyclohexenone derivative (4) which are useful as intermediates for synthesizing physiologically active materials, and a method for stereoselectively introducing substituted groups. Further, the present invention provides a method for synthesizing optically active compounds, such as optically active carvone via these intermediates.
    Type: Grant
    Filed: July 19, 1994
    Date of Patent: August 29, 1995
    Assignee: Chisso Corporation
    Inventors: Seiichi Takano, Kunio Ogasawara
  • Patent number: 5426201
    Abstract: A method of preparing manganous enolates by the treatment of alkali metal or alkaline earth metal enolates with manganous compounds in a solvent for the Mn enolate to be prepared.
    Type: Grant
    Filed: April 25, 1994
    Date of Patent: June 20, 1995
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Gerard Cahiez, Patrick Clery, Jean-Alex Laffitte
  • Patent number: 5300654
    Abstract: .beta.-hydroxyketones are prepared by reacting an aldehyde with acetone in the presence of perhydroisoindole or pyrrolidine and water. The resulting .beta.-hydroxyketone is further reacted in the presence of a solvent mixture to produce .alpha.-.beta.-unsaturated ketones.
    Type: Grant
    Filed: July 15, 1991
    Date of Patent: April 5, 1994
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Masashi Nakajima, Tadashi Kyotani, Mikio Sawaki
  • Patent number: 5258559
    Abstract: A process for the preparation of [1R-(1.beta.(R*),3a.alpha.,4.alpha.,7a.beta.)]octahydro-1-(5-hydroxy-1,5-d imethyl(hexyl)-7a-methyl-4H-inden-4-one which comprises reacting [1R-(1.beta.(R*)3a.alpha.,7a.beta.)]octahydro-1-(1,5-dimethylhexyl)-7a-met hyl-4H-inden-4-ol or [1R-(1.beta.(R*) 3a.alpha.,7a.beta.)]octahydro-1-(1,5-dimethylhexyl)-7a-methyl-4H-inden-4-o ne with sodium metaperiodate and ruthenium chloride hydrate.
    Type: Grant
    Filed: May 26, 1992
    Date of Patent: November 2, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Milan R. Uskokovic
  • Patent number: 5166450
    Abstract: This invention relates to an improved process for the production of hydroxyketones, especially dihydroxyacetone, by the condensation of one or more aldehydes in the presence of a catalyst and the use of specific process train. The product of this process is a relatively pure and any waste products from the reaction are environmentally friendly because none of the chemical components are discharged into the waste streams.
    Type: Grant
    Filed: October 4, 1991
    Date of Patent: November 24, 1992
    Assignee: BP Chemicals Limited
    Inventors: Carl A. Avison, Ian D. Dobson, Benjamin P. Gracey, Barry Hudson, Thakor Kikabhai
  • Patent number: 5166447
    Abstract: Cyclopentanones of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each an organic radical or R.sup.1 or R.sup.2 may be hydrogen and R.sup.3 is hydrogen or formyl, are prepared by a process in which a 2-formyl-3,4-dihydropyran of the general formula II ##STR2## where R.sup.1 and R.sup.2 have the abovementioned meanings, a) where R.sup.3 is formyl, is converted in the presence of an acidic heterogeneous catalyst at from 50.degree. to 500.degree. C., andb) where R.sup.3 is hydrogen,b.sub.1) is reacted with water or an alcohol in the presence of an acidic heterogeneous catalyst at from 100.degree. to 500.degree. C. in the gas phase orb.sub.2) a compound II or an acrolein of the general formula III ##STR3## is reacted with water or with water in the presence of an acid or with an alcohol in the presence of an acid at from 150.degree. to 400.degree. C. in the liquid phase. Novel 2-formylcyclopentanones are obtained.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: November 24, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Tom Witzel
  • Patent number: 5162586
    Abstract: The conjugate addition of hydrocarbon equivalents to alpha,beta-unsaturated carbonyl compounds using a series of novel catalysts is described. The catalysts comprise copper(I) complexes with ligand systems comprising either tropocoronand macrocycles or N,N'-dialkylsubstituted aminotroponeimines.
    Type: Grant
    Filed: May 9, 1989
    Date of Patent: November 10, 1992
    Assignee: Massachusetts Institute of Technology
    Inventors: Gilberto M. Villacorta, Kwang-Hyun Ahn, Stephen J. Lippard
  • Patent number: 5159117
    Abstract: A process for preparing .alpha.,.alpha.-dialkoxy ketones of the formula I ##STR1## where R.sup.1 and R.sup.2 are each, independently of one another, hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.30 -cycloalkylakyl, C.sub.9 -C.sub.30 -alkylcycloalkyl, unsubstituted or C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy-, halogen-, C.sub.1 -C.sub.4 -haloalkyl-, C.sub.1 -C.sub.4 -haloalkoxy-, phenyl-, phenoxy-, halophenyl-, halophenoxy- and/or cyano-substituted aryl, C.sub.7 -C.sub.20 -aralkyl or heterocyclyl,R.sup.2 is also ##STR2## R.sup.3 and R.sup.4 are each, independently of one another, C.sub.1 -C.sub.20 -alkyl, C.sub.3 -C.sub.20 -cycloalkyl, aryl, C.sub.7 -C.sub.20 -arylalkyl, or together are an unsubstituted or C.sub.1-C.sub.4 -alkyl- substituted C.sub.2 -C.sub.7 -alkylene chain andR.sup.5 is R.sup.1 or together with R.sup.1 is an unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted C.sub.2 -C.sub.
    Type: Grant
    Filed: August 20, 1991
    Date of Patent: October 27, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Wegner, Stefan Karbach, Hubert Smuda, Eckhard Hickmann, Reiner Kober, Rainer Seele, Thomas Zierke
  • Patent number: 5118847
    Abstract: 3-Hydroxy-2-cyclobuten-1-one salts of the general formula: ##STR1## wherein R is an ammonium group of the general formula: ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different in meaning and each is a hydrogen atom, a lower alkyl group or a cycloalkyl group or R is an alkali metal atom. The salts according for formula I are obtained by the reaction of pure 3-acetoxy-2-cyclobuten-1-one, or 1,3-cyclobutanedione or a distillation residue of the diketene production containing 3-acetoxy-2-cyclobuten-1-one, with a base. The base can be an amine of the general formula: ##STR3## wherein R.sub.1, R.sub.2, and R.sub.3 have the above-mentioned meaning, or an alkali metal alcoholate or an alkali metal hydroxide. The salts according to formula I are suitable for the production of squaric acid, by their being halogenated in a first step and then being hydrolyzed to squaric acid in a second step.
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: June 2, 1992
    Assignee: Lonza Ltd.
    Inventors: Barry Jackson, Thomas Scholl
  • Patent number: 5113021
    Abstract: A process for the manufacture of .alpha.- and .beta.-irone, namely the compounds of formula I, as well as novel intermediates in the process is provided.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: May 12, 1992
    Assignee: Givaudan Corporation
    Inventors: Georg Frater, Daniel Helmlinger
  • Patent number: 5081311
    Abstract: Muscone of the formula I ##STR1## is prepared by a process in which an open-chain 2,15-diketone of the general formula IICH.sub.3 --CO--X--CO--CH.sub.3 (II)where X is one of the radicals--(--CH.sub.2 --).sub.12 -- (a)--CH.dbd.CH--(--CH.sub.2 --).sub.8 --CH.dbd.CH-- (b)--CH.sub.2 --CH.dbd.CH--(--CH.sub.2 --).sub.6 --CH.dbd.CH--CH.sub.2 --(c)--CH.sub.2 --CH.sub.2 --CH.dbd.CH--(--CH.sub.2 --).sub.4 --CH.dbd.CH--CH.sub.2 --CH.sub.2 -- (d) or--CH.sub.2 --CH.sub.2 CH.sub.2 --CH.dbd.CH--(--CH.sub.2 --).sub.2 --CH.dbd.CH--CH.sub.2 --CH.sub.2 --CH.sub.2 -- (e)is brought into contact, at from 300.degree. to 400.degree. C. in the presence of from 5 to 15% by weight, based on the amount of catalyst, of water, in the gas phase, with a fixed-bed catalyst containing TiO.sub.2, CeO.sub.2 or the ThO.sub.2 as the catalytically active compound and the unsaturated cyclic ketone formed by intramolecular aldol condensation is subjected to catalytic hydrogenation.
    Type: Grant
    Filed: May 18, 1990
    Date of Patent: January 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Huellmann, Thomas Kuekenhoehner, Karl Brenner, Rainer Becker, Matthias Irgang, Charles Schommer
  • Patent number: 5015761
    Abstract: Novel tricycloundecanones are disclosed having the general formula ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3 are hydrogen or 1 to 3 carbon alkyl groups having a total carbon number of six or less. These compounds are useful perfumery ingredients characterized by odors of the woody type.Useful derivatives of the compounds are also disclosed as well as a novel procedure for preparation thereof.
    Type: Grant
    Filed: December 5, 1988
    Date of Patent: May 14, 1991
    Assignee: PFW(Nederland)B.V.
    Inventors: Willem Lenselink, Gerben Sipma
  • Patent number: 4929762
    Abstract: A phenol and/or a cyclohexanone is prepared by dehydrogenation of cyclohexenone and/or a cyclohexenol in liquid phase under the presence of a solid catalyst comprising a platinum-group metal loaded on a carrier. The solid catalyst comprises a carrier selected from activated carbon and hydrotalcites.
    Type: Grant
    Filed: March 2, 1989
    Date of Patent: May 29, 1990
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Fujihisa Matsunaga, Hiroshi Fukuhara
  • Patent number: 4579973
    Abstract: A novel process for the manufacture of cyclohexene derivatives which are suitable as intermediates for the manufacture of rhodoxanthin or zeaxanthin, as well as a process for the manufacture of rhodoxanthin or of zeaxanthin itself. The invention is also concerned with a novel starting material and novel intermediates in this process.
    Type: Grant
    Filed: February 8, 1985
    Date of Patent: April 1, 1986
    Assignee: Hoffman-La Roche Inc.
    Inventors: Erich Widmer, Reinhard Zell
  • Patent number: 4565894
    Abstract: Ionones are prepared by cyclization of pseudoionone with concentrated sulfuric acid in the presence of an organic solvent or diluent, while cooling, and by dilution of the reaction mixture with water, by a continuous process in which the pseudoionone is combined with an aliphatic or cycloaliphatic hydrocarbon which boils at 25.degree.-65.degree. C. under the reaction conditions, or an aliphatic chlorohydrocarbon, and the sulfuric acid, with thorough mixing and evaporative cooling by partial or complete vaporization of the solvent present in the reaction mixture, combination being effected so that the temperature of the reaction mixture is from 25.degree. to 65.degree. C. and the residence time of this mixture before it is diluted with water is from 0.5 to 20, preferably from 0.1 to 5, seconds.The novel process can be used to prepare .alpha.- and .beta.-ionone in a technically simple and advantageous manner and in very good yields.
    Type: Grant
    Filed: August 6, 1984
    Date of Patent: January 21, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Otto Hertel, Hans Kiefer, Lothar Arnold
  • Patent number: 4463194
    Abstract: A process for making piperitone from crude plinols involving hydrogenating the crude plinols to form dihydroplinols and dehydrating the dihydroplinols to yield an iridene. The iridene is then oxidatively cleaved at the unsaturation to form an acyclic dione. The dione is cyclized in the presence of a base to form piperitone.
    Type: Grant
    Filed: November 29, 1982
    Date of Patent: July 31, 1984
    Assignee: SCM Corporation
    Inventor: Tse-Lok Ho
  • Patent number: 4452813
    Abstract: A sulfonate derivative represented by the formula ##STR1## wherein R.sub.1 is lower alkyl, lower alkoxy or halogen, l is an integer of from 0 to 3, n is 0 or 1, A is straight-chain or branched-chain alkylene having 1 to 4 carbon atoms, and R.sub.2 is hydrogen or lower alkyl but, when n is 0 or 1 and A is straight-chain alkylene with 1 to 4 carbon atoms, is not hydrogen and the method for preparing the same.
    Type: Grant
    Filed: May 11, 1982
    Date of Patent: June 5, 1984
    Assignee: Taiho Pharmaceutical Company Limited
    Inventors: Setsuro Fujii, Toshihiro Hamakawa, Kazuo Ogawa, Yoshiyuki Muranaka, Sadao Hashimoto
  • Patent number: 4449007
    Abstract: A process comprising the steps of reacting 1-acetyl-3,3-dimethylcyclohexane with an alkyl acetate, thereby forming a diketone having the structure: ##STR1## reacting the said diketone with an allyl halide to form a substituted diketone having the structure: ##STR2## which is transformed into the compound having the structure: ##STR3## by means of a retro-Claisen reaction.
    Type: Grant
    Filed: November 12, 1982
    Date of Patent: May 15, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Mark A. Sprecker
  • Patent number: 4421935
    Abstract: Process for the preparation of Diels-Alder type adducts by reacting a compound with formula ##STR1## or the corresponding hydrated derivative, wherein R.sup.1, R.sup.2, and R.sup.4 are H or lower alkyl, R.sup.3 is lower alkyl, X is O,S, (O--CR.sup.5 R.sup.6 R.sup.7).sub.2 or ##STR2## wherein R.sup.5, R.sup.6 and R.sup.7 an H or lower alkyl, n is 2-5 and Y is H, alkyl or alkenyl or Y and R.sup.2 together form an alkylene group which may contain one or more substituents, with a cyclopentadiene and/or an oligomer thereof in the presence of an aqueous solution of a strong proton donor having a conjugate with a low nucleophilicity.
    Type: Grant
    Filed: May 3, 1982
    Date of Patent: December 20, 1983
    Assignee: Shell Oil Company
    Inventor: Pieter A. Verbrugge
  • Patent number: 4374275
    Abstract: Novel pyrethroid intermediates ##STR1## wherein R.sup.1 and R.sup.2 each is alkyl are prepared by treating 2,2-dimethyl-3-(2-oxopropyl)cyclopropylacetaldehyde with a trialkylsilyldialkylamine. The above compounds can be treated with ozone to form 2,3-dimethyl-3-(2-oxopropyl)cyclopropanecarbaldehyde.
    Type: Grant
    Filed: October 28, 1981
    Date of Patent: February 15, 1983
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4373108
    Abstract: Described are the compounds covered by the generic structure: ##STR1## wherein "R" represents hydrogen or lithium. The compound having the structure: ##STR2## is useful in augmenting or enhancing the patchouli aroma of a perfume, cologne or perfumed article, such as a solid or liquid anionic, cationic, nonionic or zwitterionic detergent.
    Type: Grant
    Filed: July 29, 1981
    Date of Patent: February 8, 1983
    Assignee: International Flavors & Fragrances, Inc.
    Inventors: Kenneth K. Light, Joseph A. McGhie, Futoshi Fujioka, Takao Yoshida
  • Patent number: 4347192
    Abstract: Derivatives of .alpha.,.beta.-unsaturated ketones having anticonvulsant activity and methods of their preparation from heterocyclic phosphonium salts and acyclic phosphoranes are disclosed.
    Type: Grant
    Filed: July 24, 1980
    Date of Patent: August 31, 1982
    Assignee: G. D. Searle & Co.
    Inventor: Richard A. Mueller
  • Patent number: 4338466
    Abstract: Prostaglandin analogs and process for the preparation thereof as precursors or the synthesis of oligomeric mixtures exhibiting biological activity for protection of oxidative phosphorylation of degraded mitochondria. The analogs have the general formula: ##STR1## synthesized by O-alkylating a 2-alkylcyclopentane-1,3-dione to form an enol ether, reacting the ether with CH.sub.2 .dbd.CHMgBr to form a vinyl, oxidizing the vinyl with OsO.sub.4 and NaIO.sub.4 to form an aldehyde, and reacting the aldehyde with a sodium salt of dimethyl (2-oxoalkyl)phosphonate.
    Type: Grant
    Filed: April 2, 1981
    Date of Patent: July 6, 1982
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: George L. Nelson
  • Patent number: 4336201
    Abstract: A process for the preparation of an electrically conductive polyene, wherein a polyene which contains one or more chain members of the formula where R is hydrogen or methyl, and which contains a total of not less than seven aliphatic double bonds, is treated, in the absence of moisture and of oxygen, with a strong Lewis acid having a pk.sub.a of from -10 to +4, or with an alkali metal.
    Type: Grant
    Filed: November 3, 1980
    Date of Patent: June 22, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Feichtmayr, Herbert Naarmann, Joachim Paust, Klaus Penzien
  • Patent number: 4302607
    Abstract: New unsaturated macrocyclic ketones are obtained via a process which consists in reacting a dialdehyde with a tetraalkyldiphosphonate ester. The new ketones are useful intermediates for the preparation of cyclopentadecanone and its higher methyl-homologue, known fragrant substances. New ketones possess also direct utility as musky odorants.
    Type: Grant
    Filed: September 19, 1979
    Date of Patent: November 24, 1981
    Assignee: Firmenich SA
    Inventors: George H. Buchi, Hans Wuest
  • Patent number: 4302363
    Abstract: This invention is directed to the isomer mixture 4(5)-acetyl-7,7,9(7,9,9)-trimethylbicyclo[4.3.0]non-1-ene, the preparation thereof, and the use of said mixture as a perfuming agent. The isomer mixture represents a valuable new perfuming agent having strong, warm ambergris scent with woody tobacco leaf, methyl ionone, and arborvitae notes and having exceptional persistence as well.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: November 24, 1981
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Klaus Bruns, Ursula Weber
  • Patent number: 4292432
    Abstract: A process for producing novel aldol derivatives of the formula, ##STR1## wherein C=W is a carbonyl group or a protected carbonyl group which comprises reacting a compound of the formula: ##STR2## wherein C=W is as defined above in the presence of an acid or a base at a temperature ranging from -70.degree. C. to room temperature. The novel aldol derivatives of the above formula are useful as intermediate for producing methanoprostacyclin derivatives which are useful medicines for prevention of thrombosis.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: September 29, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Ono, Akihiko Sugie, Hajime Kawakami, Junki Katsube
  • Patent number: 4288613
    Abstract: A method of synthesis of cyclopentanones comprising cyclizing a 4-pentenal, preferably under an ethylene atmosphere, in the presence of a catalytically effective amount of a cyclizing, rhodium(I) para-substituted triarylphosphine catalyst.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: September 8, 1981
    Assignee: Iowa State University Research Foundation, Inc.
    Inventor: Richard C. Larock
  • Patent number: 4287081
    Abstract: Described is a process for augmenting or enhancing the aroma of a solid or liquid anionic, cationic or nonionic detergent comprising the step of adding in an aroma augmenting or enhancing quantity to a solid or liquid anionic, cationic or nonionic detergent base at least one tricyclic ketone having the structure: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and each represents hydrogen or C.sub.1 --C.sub.3 lower alkyl.
    Type: Grant
    Filed: October 23, 1980
    Date of Patent: September 1, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, James M. Sanders, William L. Schreiber, Hugh Watkins, Joaquin F. Vinals, Edward J. Shuster, Thomas J. O'Rourke, Myrna L. Hagedorn, Philip Klemarczyk
  • Patent number: 4281204
    Abstract: The present invention relates to substituted spirocyclic derivatives having the general formula: ##STR1## wherein the dotted line represents a carbon-carbon double bond or a carbon-carbon single bond, wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are each the same or different, hydrogen or lower alkyl, wherein Z is one of the following: ##STR2## wherein R.sub.7 is either hydrogen or lower alkyl, wherein R.sub.8 and R.sub.9 are each lower alkyl; their methods of preparation and their use as odor-modifying ingredients in perfumes and perfumed products, and as flavor-modifying ingredients in the flavoring of foodstuffs and tobacco products.
    Type: Grant
    Filed: October 5, 1979
    Date of Patent: July 28, 1981
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Robert G. Eilerman
  • Patent number: 4250338
    Abstract: Described are compounds covered by the generic structure; ##STR1## where one, two or all of R.sub.1, R.sub.2 and R.sub.3 are the same or different and each represents hydrogen or lower alkyl of from 1 up to 3 carbon atoms; a process for preparing same using compounds having the generic structure; ##STR2## where one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines represents carbon-carbon single bonds and organoleptic uses thereof in perfumes, colognes, perfumed articles such as anionic, cationic and non-ionic detergents, cosmetic powders and dryer-added fabric softener articles, as well as in smoking tobaccos and smoking tobacco articles, e.g., the body of smoking tobacco, the wrapper or the filter therefor.
    Type: Grant
    Filed: November 16, 1979
    Date of Patent: February 10, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, James M. Sanders, William L. Schreiber, Hugh Watkins, Joaquin F. Vinals, Edward J. Shuster, Thomas J. O'Rourke, Myrna L. Hagedorn, Philip Klemarczyk
  • Patent number: 4247711
    Abstract: 2-Formyl-3,3-dimethylcyclopropylacetic acid is prepared by ozonolysis of 3-acetyl-6,6-dimethylbicyclo[3.1.0]-2-hexene followed by reductive cleavage of the ozonolysis product thus formed. The 3-acetyl-6,6-dimethylbicyclo[3.1.0]-2-hexene is prepared by contacting 2-(2-acetyl-3-oxobutyl)-3,3-dimethylcyclopropanecarbaldehyde with a base in the presence of a solvent.
    Type: Grant
    Filed: April 24, 1979
    Date of Patent: January 27, 1981
    Assignee: Shell Oil Company
    Inventors: Pieter A. Verbrugge, Petrus A. Kramer
  • Patent number: 4204073
    Abstract: A process for producing trimethyl oxo or hydroxy substituted cycopentenone food coloring agents including intermediates in this process.
    Type: Grant
    Filed: April 6, 1979
    Date of Patent: May 20, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Frank Kienzle
  • Patent number: RE32721
    Abstract: Described are compounds covered by the generic structure. ##STR1## where one, two or all of R.sub.1, R.sub.2 and R.sub.3 are the same or different and each represents hydrogen or lower alkyl of from 1 up to 3 carbon atoms; a process for preparing same using compounds having the generic structure; ##STR2## where one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines represents carbon-carbon single bonds and organoleptic uses thereof in perfumes, colognes, perfumed articles such as anionic, cationic and non-ionic detergents, cosmetic powders and dryer-added fabric softener articles, as well as in smoking tobaccos and smoking tobacco articles, e.g., the body of smoking tobacco, the wrapper or the filter therefor.
    Type: Grant
    Filed: December 21, 1984
    Date of Patent: July 26, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, James M. Sanders, William L. Schreiber, Hugh Watkins, Joaquin F. Vinals, Edward J. Shuster, Thomas J. O'Rourke, Myrna L. Hagedorn, Philip Klemarczyk