Unsaturated Alicyclic Ring Containing Patents (Class 568/667)
-
Patent number: 5731283Abstract: Described are 1(4'-methylpentyl)-4-substituted ethylcyclohexane derivatives defined according to the structure: ##STR1## wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different hydrogen or methyl; wherein the dashed line represents a carbon carbon single bond or a carbon carbon double bond; wherein the wavy line represents a carbon carbon single bond or a carbon carbon double bond; with the proviso that when the wavy line is a carbon carbon single bond then the dashed line is a carbon carbon single bond; wherein Y represents a moiety selected from the group consisting of: ##STR2## wherein H represents hydrogen, C.sub.1 -C.sub.4 lower alkyl or C.sub.1 -C.sub.2 acyl; and wherein R.sub.1 represents C.sub.1 -C.sub.4 lower alkyl with the additional proviso that when Y is the moiety: ##STR3## then the dashed line is a carbon carbon single bond, and uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, perfumed articles and colognes.Type: GrantFiled: January 28, 1997Date of Patent: March 24, 1998Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, James Joseph Koestler, Jan Van Elst
-
Patent number: 5698136Abstract: A novel liquid crystalline compound having a high elastic constant ratio, K.sub.33 /K.sub.11, a superior compatibility with other liquid crystal compounds, particularly a low temperature compatibility therewith, and chemical stability; a liquid crystal composition containing such a liquid crystalline compound; and a liquid crystal display element, are provided,which liquid crystalline compound is expressed by the formula (1) ##STR1## wherein R.sub.1 is an alkyl group or an alkyloxy group of 1 to 10C or a halogenated alkyl group, a halogenated alkyloxy group of 1 to 4C, halogen atom or cyano group; R.sub.2 is H atom or an alkyl group of 1 to 3C; rings A and B each independently are 1,4-phenylene ring or trans-1,4-cyclohexylene group, which may be substituted by halogen atom; Z is single bond, 1,4-phenylene ring, trans-1,4-cyclohexylene ring or 1,2-ethylene group; p is 2 to 4; and q is 0 or 1.Type: GrantFiled: February 22, 1996Date of Patent: December 16, 1997Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Shuichi Matsui, Norihisa Hachiya, Etsuo Nakagawa
-
Patent number: 5672779Abstract: The present invention provides a compound represented by the formula: ##STR1## wherein R.sub.1 denotes a hydrogen atom or a methyl group; R.sub.2 represents a 1-methyl-2-propenyl group, a 1-methyl-2-propynyl group, a 3,3-dihalogeno-1-methyl-2-propenyl group or a C.sub.1 -C.sub.6 alkyl group which may be substituted with at least one halogen atom; and A' represents a hydrogen atom or a protecting group for a hydroxyl group. The compound is useful in the preparation of esters which can be used to control insect pests.Type: GrantFiled: May 1, 1996Date of Patent: September 30, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Tomonori Iwasaki, Masaya Suzuki, Takashi Furukawa, Kazunori Tsushima, Takao Ishiwatari, Toru Tsuchiya
-
Patent number: 5629454Abstract: Conformationally locked 4',6'-cyclopropane-fused carbocyclic nucleoside analogues. The compounds are prepared by condensing a cyclopropane-fused carbocyclic allylic alcohol with substituted purine or pyrimidine bases. The condensation products are then modified to produce the adenosine, guanosine, cytidine, thymidine and uracil nucleoside analogues. The compounds are therapeutically useful as antimetabolites, or in the preparation of anti-metabolic agents.Type: GrantFiled: September 23, 1994Date of Patent: May 13, 1997Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Victor E. Marquez, Juan B. Rodriguez, Marc C. Nicklaus, Joseph J. Barchi, Jr., Maqbool A. Siddiqui
-
Patent number: 5552434Abstract: Compounds of the formula ##STR1## where the dotted line represents a bond or the absence of a bond, the wavy lines represent bonds which are either in cis or trans configuration; R.sub.1 represents H, or CO--R.sub.2 where R.sub.2 is lower alkyl of 1 to 6 carbons, carbocyclic aryl or heterocyclic aryl; or carbocyclic aryl or heteroaryl substituted lower alkyl group; X represents CO--NR.sub.3 R.sub.4, CH.sub.2 OH, CH.sub.2 OR.sub.5, CH.sub.2 O--COR.sub.6, and CH.sub.2 --NR.sub.3 R.sub.4, where R.sub.3 and R.sub.4 independently are H or lower alkyl, R.sub.5 is lower alkyl of 1 to 6 carbons, and R.sub.6 is lower alkyl of 1 to 6 carbons, carbocyclic aryl or heterocyclic aryl; or carbocyclic aryl or heteroaryl substituted lower alkyl group, and n is an integer between 0 and 8 are capable of lowering intraocular pressure in the eye of a mammal.Type: GrantFiled: December 14, 1994Date of Patent: September 3, 1996Assignee: AllerganInventors: Michael E. Garst, Robert M. Burk
-
Patent number: 5405948Abstract: A compound of formula (I): selected from 1,5-diyne-3-cyclodecene and undecene compounds. ##STR1## in which: R represents a hydrogen atom, a straight-chain or branched (C.sub.1 -C.sub.6) acyl radical or a glycoside radical,R' represents a hydrogen atom ##STR2## n is 1 or 2, and R.sub.1 and R.sub.2 simultaneously represent two hydrogen atoms or, together with the two carbon atoms and the double bond to which they are attached, form a phenyl ring.Type: GrantFiled: September 30, 1992Date of Patent: April 11, 1995Assignee: Adir et CompagnieInventors: Jean-Marie Beau, Christophe Crevisy, Ghanem Atassi, Alain Pierre
-
Patent number: 5362916Abstract: Hydroxyaryl enol ether alkali metal salts having the formula: ##STR1## in which T is a fused, substituted or unsubstituted polycycloalkylidene group, OR.sup.3 is an ether group Y is a light-emitting fluorophore-forming group which will be part of a luminescent substance formed by decomposition of a 1,2-dioxetane subsequently formed from the hydroxyaryl enol ether alkali metal salt, capable of absorbing energy to form an excited state from which it emits optically detectable energy to return to its ground state, and AM.sup.30 is an alkali metal cation, processes for the preparation of these intermediate salts, and their use as starting materials for acylation, phosphorylation and glycosylation reactions to give intermediates reactable to give stable, water-soluble chemiluminescent 1,2-dioketames, particularly ones that are enzymatically cleavable, are disclosed.Type: GrantFiled: November 17, 1993Date of Patent: November 8, 1994
-
Patent number: 5321164Abstract: Described is the 2(1-vinyl-5-hexenyl)cyclopentanone having the structure: ##STR1## a process for preparing same by reacting the compound having the structure: ##STR2## with the compound having the structure: ##STR3## and then heating the resulting intermediate, and organoleptic uses of the compound having the structure: ##STR4## in perfumery.Type: GrantFiled: October 27, 1993Date of Patent: June 14, 1994Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, William J. Fylak, Joseph A. Mc Ghie, Charles E. J. Beck
-
Patent number: 5313002Abstract: The invention relates to novel ethers and their use as aroma precursors. The ethers are derived from ionol and related compounds. These aroma precursors do not have a substantial aroma as such under ambient conditions, but will break up into a complex mixture having useful organoleptic properties under heating. The ethers are especially suitable for use in products which are heated, burned or smouldered in some stage of their use. The compounds according to the invention are especially suitable for application to tobacco. Mixtures obtained by degrading (e.g. by heating) the ethers according to the invention may be used in a flavouring or perfuming mixture as well due to their organoleptic properties.Type: GrantFiled: November 3, 1992Date of Patent: May 17, 1994Assignee: Unilever Patent Holdings B.V.Inventors: Johannes T. De Heij, Franciscus P. Van Lier, Harrie Renes
-
Patent number: 5288428Abstract: Compounds having a terminal alkyloxypropenyl group of the general formula ##STR1## wherein rings A.sup.1 and A.sup.2 each independently represent unsubstituted or halogen-substituted 1,4-phenylene, in which optionally 1 CH group or 2 CH groups is/are replaced by nitrogen, or trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl; n is either 0 or 1; Z.sup.1 and Z.sup.2 each independently signify a single covalent bond or --CH.sub.2 CH.sub.2 --, --COO--, --OOC--, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O--, the trans form of --O--CH.sub.2 --CH.dbd.CH--, --CH.dbd.CH--CH.sub.2 --O--, --(CH.sub.2).sub.2 CH.dbd.CH-- or --CH.dbd.CH--(CH.sub.2).sub.2 --; R.sup.1 denotes an alkyl group; R.sup.2 represents halogen, cyano, trifluoroacetyl, optionally fluorine-substituted alkyl with 1 to 12 carbon atoms, in which optionally 1 --CH.sub.2 -- group or 2 non-adjacent --CH.sub.2 -- groups is/are replaced by oxygen and/or a --CH.sub.2 CH.sub.Type: GrantFiled: August 6, 1991Date of Patent: February 22, 1994Assignee: Hoffmann-La Roche Inc.Inventor: Stephen Kelly
-
Patent number: 5243094Abstract: Derivatives of long-chain fatty alcohols, and methods of obtaining them, are provided, as well as pharmaceutical compositions containing derivatives and their uses, in particular in treating or preventing neuro-degenerative illnesses, conditions linked to skin ageing, the phenomena of thrombosis and atherosclerosis, and immune deficiencies.Type: GrantFiled: July 11, 1991Date of Patent: September 7, 1993Assignee: MedaforInventor: Jacques Borg
-
Patent number: 5243080Abstract: The present invention provides a novel compound represented as ##STR1## The present novel compound is prepared by reacting fluorine with pyridine-boron trifluoride and is useful as a fluorinating agent in the fluorination of organic compounds.Type: GrantFiled: July 8, 1992Date of Patent: September 7, 1993Assignee: AlliedSignal Inc.Inventors: Michael Van Der Puy, David Nalewajek, George A. Shia, William J. Wagner
-
Patent number: 5227507Abstract: A process for the manufacture of compounds of the general formula ##STR1## wherein R.sup.1 signifies hydroxy or an etherified hydroxy group, and of zeaxanthin by converting a compound of the general formula ##STR2## wherein R.sup.1 has the above significance, in an inert organic solvent into the acetylenide and reacting this with methyl vinyl ketone, reducing the alcoholate obtained or the alcohol (obtained after hydrolysis of the alcoholate) of the general formula ##STR3## wherein R.sup.1 has the above significance, in an inert organic solvent with an aluminum hydride of the general formulaR.sub.x MAlH.sub.4-x IIIwherein M signifies alkali metal, R represents C.sub.1 -C.sub.10 -alkoxy or a group of the formula C.sub.n H.sub.2n+1 --O--C.sub.m H.sub.2m --O--, m and n each individually denote whole numbers of 1 to 7 and x stands for 0, 1, 2 or 3,and subsequently hydrolyzing to give the compound of formula IV and, if desired, converting the compound of formula IV obtained into zeaxanthin.Type: GrantFiled: March 23, 1990Date of Patent: July 13, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Teodor Lukac, Milan Soukup
-
Patent number: 5225608Abstract: The present invention relates to novel substituted cyclohexanol compounds possessing a sandalwood aroma which are useful as fragrance materials. The invention also provides methods for synthesis thereof through a novel aldehyde intermediate. The compounds of the invention have the formula: ##STR1## wherein A is ##STR2## and wherein R.sub.1 is methyl or ethyl, R.sub.2 -R.sub.7 are independently hydrogen or methyl with the proviso that a maximum of two of the substituents R.sub.2 -R.sub.7 are methyl, and R.sub.8 is hydrogen, lower alkyl (C.sub.1 to C.sub.5) or acyl. The invention also provides fragrance compositions which utilize the compounds of the invention to impart a sandalwood aroma to perfume compositions, colognes and perfumed articles.Type: GrantFiled: August 6, 1991Date of Patent: July 6, 1993Assignee: BASF K & F CorporationInventors: Robert Eilerman, Philip Christenson, John Yurecko, Jr., Thomas Zebovitz
-
Patent number: 5208357Abstract: There are provided enantiomerically enhanced chiral substituted cyclopentadienyl ligands and compounds thereof, and a process for their making comprising contacting a substituted fulvene or derivative thereof with an enantiomerically enhanced or pure nucleophile having at least one chiral center. There are further provided enantiomerically enhanced chiral organometallic complexes having one or more chiral substituted cyclopentadienyl groups.Type: GrantFiled: December 31, 1990Date of Patent: May 4, 1993Assignee: Exxon Chemical Patents, Inc.Inventor: Eric A. Mintz
-
Patent number: 5187286Type: GrantFiled: March 25, 1991Date of Patent: February 16, 1993Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt
-
Patent number: 5185472Abstract: Novel mixtures of bicyclic ethers of the formulas ##STR1## wherein R represents an alkyl group of from one to four carbon atoms, said mixture having at least a 1.1:1 ratio of Ia to Ib, a process for their manufacture and their use as odoranis and novel intermediates for their preparation are described.Type: GrantFiled: February 28, 1991Date of Patent: February 9, 1993Assignee: Givaudan CorporationInventors: Georg Frater, Harald Schmidt
-
Patent number: 5177245Abstract: Provided is a process for preparing optionally-substituted cyclohexenylhydroquinones starting from cyclohexanone.Type: GrantFiled: November 25, 1991Date of Patent: January 5, 1993Assignee: Eastman Kodak CompanyInventors: Dewey W. Fuller, Jr., Gether Irick, Jr.
-
Patent number: 5137921Abstract: There is provided an inhibitory agent of an increase in blood sugar level, comprising conduritol A of the formula(I): ##STR1## or a derivative thereof, as an active component.Type: GrantFiled: July 26, 1991Date of Patent: August 11, 1992Assignee: Dai-Nippon Sugar Mfg. Co., Ltd.Inventors: Ituo Kensho, Fumio Yamashita, Toshikazu Nagai, Tadashi Fujimoto, Yoshihisa Nakano, Hideki Tukimura
-
Patent number: 5087775Abstract: A process for the preparation of partially fluorinated alcohols starting from halogen-containing alkenes, and 2,2,3,3,4,4-hexafluorocyclopentanol as a new partially fluorinated alcohol.Type: GrantFiled: October 24, 1990Date of Patent: February 11, 1992Assignee: Bayer AktiengesellschaftInventors: Karl-Rudolf Gassen, Dietmar Bielefeldt, Michael Negele, Heinz Ziemann
-
Patent number: 4978806Abstract: A method for preparation of 1-methoxycyclohepta-1,3,5-triene in commercial quantities, which comprises the steps of heating 7,7-dichloro-1-methoxybicyclo[4.1.0]heptane in a refluxing reaction solvent comprising a lower boiling aromatic amine, at reflux, until suitable amounts of 1-methoxycyclohepta-1,3,5-triene have been produced, and recovering the 1-methoxycyclohepta-1,3,5-triene. Suitable reaction solvents include 2-picoline, pyridine and 2,6-lutidine. The method according to the present invention results in safer temperature control in the production of 1-methoxycyclohepta-1,3,5-triene, and increased yields.Type: GrantFiled: November 27, 1989Date of Patent: December 18, 1990Assignee: Her Majesty the Queen in right of Canada, as represented by the Minister of National Defence of Her Majesty's Canadian GovernmentInventor: Gordon E. Langford
-
Patent number: 4948780Abstract: Compounds of the general formulae ##STR1## in which R may be a methyl or ethyl radical and R.sup.1 may be a hydrogen, methyl or ethyl radical are disclosed. Also provided as part of the present invention are processes for the preparation of the above compounds. The compounds of the invention are useful as scents.Type: GrantFiled: January 6, 1988Date of Patent: August 14, 1990Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Walter Hafner, Helmut Gebauer, Erich Markl, Marlies Regiert
-
Patent number: 4891451Abstract: Vinyl ethers of the formula (I) ##STR1## where R.sup.1 to R.sup.3 are identical or different and are each hydrogen, a straight-chain or branched alkyl or alkenyl radical of not more than 12 carbon atoms, halogen-substituted alkyl, a cycloalkyl or cycloalkenyl radical of 5 to 8 carbon atoms, an aryl, alkylaryl, alkenylaryl, aralkyl or aralkenyl radical of 6 to 16 carbon atoms, halogen-substituted aryl or a heterocyclic radical and furthermore R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3, together with the carbon atom to which they are bonded, may form a cycloalkane, cycloalkene or heterocyclic structure, and R.sup.4 is alkyl, alkylaryl or aralkyl, are prepared by a process in which an alcohol is eliminated from an acetal or ketal of the formula (II) ##STR2## where R.sup.1 to R.sup.4 have the above meanings, in the presence of borosilicate and/or iron silicate zeolites as catalysts.Type: GrantFiled: June 30, 1988Date of Patent: January 2, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
-
Patent number: 4792637Abstract: A process for the synthesis of vinyl ethers of formula ##STR1## wherein R.sub.1 and R.sub.2, each independently, represent hydrogen or a primary, secondary or tertiary alkyl group,R.sub.3 is a hydrogen, a primary alkyl, phenyl, or substituted phenyl group, orR.sub.2 and R.sub.3, taken together, represent a polymethylene chain containing from 3 to 10 carbon atoms wherein one or more hydrogens can be replaced by methyl or ethyl groups, andR is a primary, secondary or tertiary alkyl group, which comprises reacting a suitably selected dioxolane derivative of formula II ##STR2## wherein R.sub.1, R.sub.2, and R.sub.3 are as defined above, andR.sub.4, R.sub.5, R.sub.6, and R.sub.7, each independently, represent hydrogen or an alkyl group, with a boric acid ester of formula IIIB(OR).sub.3 IIIwhereinR is as defined above, in the vapor phase, at a temperature comprised between 100.degree. and 400.degree. C., and in the presence of an acidic heterogeneous catalyst.Type: GrantFiled: July 17, 1987Date of Patent: December 20, 1988Assignee: Enichem Anic SpAInventors: Giuseppe Messina, Mario D. Moretti, Salvatore R. Sanna, Giovanni Soma, Pier G. Cabras
-
Patent number: 4703127Abstract: Compounds of the general formula I are disclosed as useful intermediates in the preparation of prostanoids: ##STR1## wherein A represents O or H, OR.sup.z ;R.sup.z represents hydrogen or a protecting group;R.sup.x represents hydrogen or a protecting group; andR.sup.y represents halogen, a substituted thio group, di-substituted amino group, or a group of the formula R.sup.2, and R.sup.2 represents a straight- or branched-chain alkyl alkenyl or alkynyl group which may optionally be substituted by one or more carboxyl, carboxylic acid ester, or free or protected hydroxyl, thiol, aldehyde or keto groups;with the provisos that R.sup.x is not hydrogen when A is O and R.sup.y is R.sup.2 ; and that when A is H, OR.sup.z R.sup.y and R.sup.2 and R.sup.x and R.sup.z are not both hydrogen.Processes for the preparation of these compounds and of 2-substituted 4-hydroxy-cyclopent-2-en-1-one derivatives are also disclosed.Type: GrantFiled: September 2, 1983Date of Patent: October 27, 1987Assignee: The Australian National UniversityInventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
-
Patent number: 4614747Abstract: This invention relates to novel compounds having pharmaceutical activity and having the general structure ##STR1## wherein the Z, R.sub.1, R.sub.2, R.sub.3, R.sub.4, n and m are defined within.Type: GrantFiled: November 29, 1984Date of Patent: September 30, 1986Assignee: USV Pharmaceutical Corp.Inventors: Bernard Loev, Howard Jones, Wan-kit Chan
-
Patent number: 4608445Abstract: The compounds of formulaX--CH.sub.2 --CH(OH)--CH.sub.2 --R (I)wherein symbol R represents a C.sub.1 -C.sub.3 alkyl radical and X a substituted cyclohexyloxy group of formula ##STR1## wherein index n stands for zero or one, the dashed lines indicate a single bond (n=1) or a double bond in position 2 (n=0) or 3 (n=1) and each of symbols R.sup.1 to R.sup.6 designates a hydrogen atom or a methyl radical, are new and can be conveniently utilized as perfuming and flavoring ingredients. They develop in particular woody-ambery notes.Type: GrantFiled: November 23, 1982Date of Patent: August 26, 1986Assignee: Firmenich SAInventors: Wolfgang K. Giersch, Karl H. Schulte-Elte, Gunther Ohloff
-
Patent number: 4604480Abstract: A method for the preparation of a first sulfone compound of the formula: ##STR1## wherein R.sub.a is ##STR2## where R.sub.b is Br and R.sub.c is H except that R.sub.b and R.sub.c together may be an electron pair when R.sub.6 is a radical of the formula: ##STR3## wherein X.sub.1 is independently chlorine, bromine or iodine and R.sub.1 and R.sub.2 are independently at each occurrence hydrogen or, substituted or unsubstituted, phenyl or alkyl where the substituents are halogen or alkoxy or additional --SO.sub.2 Br groups; provided that, each carbon atom of R.sub.1 or R.sub.2 which contains --SO.sub.2 Br also contains an X.sub.1 group and wherein R.sub.3 through R.sub.9 are independently --OZ,--C.sub.6 M.sub.5,--Z,--SiZ.sub.3 or --X.sub.2, where Z is hydrogen or substituted or unsubstituted phenyl, alkyl, alkenyl or alkynyl; X.sub.2 is chlorine, bromine, iodine or fluorine; M is independently at each occurrence Z or X.sub.2 ; R.sub.3 and R.sub.4 may together be an electron pair; two or more of R.sub.3, R.sub.Type: GrantFiled: August 15, 1983Date of Patent: August 5, 1986Assignee: The Research Foundation of State University of New YorkInventors: Eric Block, Mohammad Aslam
-
Patent number: 4601851Abstract: Cyclododec-2-enyl ethers having the formula ##STR1## wherein R is a straight or branched chain C.sub.1-4 alkyl or alkenyl group, have fragrance characteristics similar to patchouli oil, and are attractive compounds for use in the manufacture of fragrance compositions.Type: GrantFiled: January 9, 1984Date of Patent: July 22, 1986Assignee: Huels AktiengesellschaftInventors: Martin Bartmann, Klaus Burzin
-
Patent number: 4593142Abstract: Catalysts comprising mixtures of HF and metal alkoxides and mixed metal alkoxides produce a sharply peaked alkoxylation distribution during the alkoxylation of organic materials.Type: GrantFiled: February 21, 1984Date of Patent: June 3, 1986Assignee: Vista Chemical CompanyInventor: Kang Yang
-
Patent number: 4533760Abstract: Olefins are produced by contacting an organic compound having at least one benzene ring with calcium metal, ethylenediamine, a low molecular weight aliphatic alcohol, and optionally a low molecular weight aliphatic primary amine, and/or an inert, abrasive particulate substance. The reduction is conducted at temperatures ranging from about -10.degree. C. to about 30.degree. C. or somewhat higher. Substantially all of the organic compounds are converted to corresponding cyclic olefins, primarily diolefins.Type: GrantFiled: August 23, 1984Date of Patent: August 6, 1985Assignee: Purdue Research FoundationInventors: Robert A. Benkeser, James A. Laugal, Angela Rappa
-
Patent number: 4533752Abstract: Olefins are produced by containing an organic compound having at least one benzene ring with ethylenediamine and calcium metal, the calcium metal being used in large excess or alternatively in conjunction with an inert abrasive particulate substance. Substantially all of the organic compounds are converted to corresponding cyclic olefins, largely mono-olefins.Type: GrantFiled: August 23, 1984Date of Patent: August 6, 1985Assignee: Purdue Research FoundationInventors: Robert A. Benkeser, James A. Laugal, Angela Rappa
-
Patent number: 4506102Abstract: 2-Methoxyethyl cyclododec-1-enyl ether is of interest as a precursor for the saturated ether, 2-methoxyethyl cyclododecyl ether, which can be obtained therefrom by catalytic hydrogenation, in a high purity and with a good fragrance quality. The saturated ether is a valuable fragrance component having a woody note. A process for producing 2-methylethyl cyclododec-1-enyl ether comprises the step of reacting cyclododecanone, 2-methoxyethanol and a tri(lower alkyl) orthoformate, at a temperature of 50.degree.-250.degree. C., in the presence of an acid catalyst, removing resultant low-boiling compounds by distillation, and recovering resultant 2-methoxyethyl cyclododec-1-enyl ether.Type: GrantFiled: May 27, 1983Date of Patent: March 19, 1985Assignees: Chemische Werke Huls AG, Naarden International N.V.Inventors: Manfred Kaufhold, Hendrik J. Takken
-
Patent number: 4396781Abstract: New compounds of formula ##STR1## wherein symbol R represents a lower alkyl radical and use thereof as perfuming and flavoring ingredients. Process for the preparation of the said compounds.Type: GrantFiled: November 30, 1979Date of Patent: August 2, 1983Assignee: Firmenich SAInventors: Wolfgang Giersch, Gunther Ohloff
-
Patent number: 4326996Abstract: The present invention relates to substituted cyclohexane derivatives having the structure: ##STR1## wherein the dotted line may be 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,R.sub.6,R.sub.7 and R.sub.8 may be hydrogen or lower alkyl; wherein Z may be any of the following: ##STR2## wherein R.sub.9 may be hydrogen or lower alkyl; and wherein R.sub.10 and R.sub.11 are lower alkyl. This invention also provides methods of preparing and using the compounds as odor-modifying ingredients in perfumes and perfumed products, and as flavor-modifying ingredients in foodstuffs and tobacco products.Type: GrantFiled: January 30, 1980Date of Patent: April 27, 1982Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Robert G. Eilerman
-
Patent number: 4310709Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.Type: GrantFiled: April 23, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
-
Patent number: 4262145Abstract: A process for converting an olefin, or a mixture of olefins, to an ether, or a mixture of ethers, which comprises reacting said olefin, or said mixture of olefins, with an alkanol in contact with silicatungstic acid.Type: GrantFiled: December 10, 1979Date of Patent: April 14, 1981Assignee: Gulf Research & Development CompanyInventors: Charles M. Selwitz, John G. McNulty
-
Patent number: 4249025Abstract: An improved multi-step process for synthesizing the liquid irritant 1-metycycloheptatriene from tropylium tetrafluoborate the improvement comprising the step of using a polymerization/condensation inhibitor or retarder to minimize impurities and increase yield of the irritant product. Phenothiazine is the preferred polymerization inhibitor.Type: GrantFiled: April 28, 1978Date of Patent: February 3, 1981Assignee: The United States of America as represented by the Secretary of the ArmyInventor: William R. Hydro
-
Patent number: 4230823Abstract: The instant invention is directed to a process for the preparation of modified polyether polyols comprising polymerizing of from 1 to 50 parts by weight of a mixture of 20 to 100% by weight (based on the total quantity of monomers) of acrylonitrile and 0 to 80% by weight of styrene in 50 to 99 parts by weight of the polyether polyol in the presence of a polymerization initiator which yields radicals, wherein said polymerization is carried out in the presence of from 0.1 to 1.5% by weight, based on the total quantity of monomers put into the process, of a compound of the formula:A=CH--X--RwhereinA represents a divalent group ##STR1## R represents a C.sub.1-18 alkyl, C.sub.1-10 cycloalkyl, or substituted or unsubstituted benzyl group,R' represents C.sub.1-8 alkyl group,n represents 0, 1 or 2 andX represents oxygen or sulfur.Type: GrantFiled: August 9, 1979Date of Patent: October 28, 1980Assignee: Bayer AktiengesellschaftInventors: Heinrich Alberts, Gerhard Balle
-
Patent number: 4169073Abstract: Described are perfume and cologne compositions containing the compound 3(2-chloroalkyloxy).sub.2 (10) pinene.This is a divisional of application Ser. No. 872,937, filed Jan. 27, 1978, now U.S. Pat. No. 4,131,687.Type: GrantFiled: September 5, 1978Date of Patent: September 25, 1979Assignee: International Flavors & Fragrances Inc.Inventors: Cynthia J. Mussinan, Braja D. Mookherjee, Manfred H. Vock, Frederick L. Schmitt, Edward J. Shuster, James M. Sanders, Bette M. Light, Edward J. Granda
-
Patent number: 4160109Abstract: Cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals of the formula ##STR1## wherein each R is a primary or secondary C.sub.1-4 alkyl radical are obtained by catalytic hydrogenation of p-benzoquinone tetramethyl-diketal with about 1 mol of H.sub.2 per mole of diketal, in a basic medium, at a temperature of from about -10.degree. to +150.degree. C. and optionally by reketalization with a primary or secondary C.sub.2-4 alcohol in a slightly acid medium with substantial exclusion of water, at a temperature of from about -10.degree. to +35.degree. C. Cyclohexene-(1)-dione-(3,6)-tetraalkyldiketals, optionally dissolved in an alcohol ROH give hydroquinone dialkyl ethers on acidification and heating to about 60.degree. to 120.degree. C., which ethers are valuable dyestuff intermediates.Type: GrantFiled: January 26, 1978Date of Patent: July 3, 1979Assignee: Hoechst AktiengesellschaftInventor: Rudolf Pistorius
-
Patent number: 4159998Abstract: Disclosed is an improved process for the preparation of 2-(7-hydroxyalkyl)-4R, 4S or 4RS -hydroxy-cyclopent-2-enone corresponding to the formula ##STR1## wherein m is an integer from 2 to 4. The compounds prepared by this process are useful as precursors in the preparation of carbinol PGE.sub.1 analogues having utility as bronchodilators and inhibitors of gastric secretion.Type: GrantFiled: September 11, 1978Date of Patent: July 3, 1979Assignee: Miles Laboratories, Inc.Inventor: Harold C. Kluender
-
Patent number: 4156097Abstract: Bis-(2-cyclopentenyl) ethers are prepared by contacting a 2-cyclopentenyl carboxylate or 2-cyclopentenol with an aqueous acid solution having a pH in the range of about 1.0 to about 3.0.Type: GrantFiled: August 1, 1978Date of Patent: May 22, 1979Assignee: Union Carbide CorporationInventors: Benjamin Phillips, Walter J. Skraba
-
Patent number: 4132726Abstract: Novel optically active compounds of 4-protected hydroxy-cyclopent-2-en-1-ones of the formula ##STR1## wherein R is a splittable protective group for an alcoholic hydroxyl group, and a process for preparing the 4-protected hydroxycyclopent-2-en-1-ones by oxidizing monohydroxy-protected derivatives of cyclopent-1-ene-3,5-diol expressed by the following formula ##STR2## wherein R is the same as defined above. Optically active 4-hydroxycyclopent-2-en-1-one which is an optically active isomer of the compound of formula (2); or optically active cyclopent-1-en-3,5-diol (R-isomer) and a novel diacyl derivative of the diol, a novel monoacylmonosilyl-derivative of the diol and a novel monoacylmonotetrahydropyranol-derivative of the diol, which are intermediates for the protective derivative of formula (1). Processes are also provided for preparing the protective derivatives of formula (1) by converting these intermediates by esterification, hydrolysis, enzymatic processes, etc.Type: GrantFiled: December 22, 1975Date of Patent: January 2, 1979Assignee: Teijin LimitedInventors: Seizi Kurozumi, Takeshi Toru, Toshio Tanaka, Shuzi Miura, Makiko Kobayashi, Sachio Ishimoto, Sadakazu Matsubara
-
Patent number: 4131687Abstract: Described are processes and compositions for augmenting or enhancing the flavor and/or aroma of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, perfumes, colognes, and perfumed articles using as the essential ingredient at least one C.sub.10 -terpene alkyl, alkenyl, haloalkenyl, and alkynyl ether and diether having the formula:(C.sub.10 -TERPENYL) (O-R.sub.1).sub.nwherein n is 1 or 2; the terpene group is a moiety having one of the structures: ##STR1## AND R.sub.1 is one of C.sub.1 -C.sub.4 alkyl, C.sub.3 or C.sub.4 alkenyl, C.sub.3 alkynyl, or C.sub.3 haloalkenyl. The compounds wherein R.sub.1 is C.sub.2 -C.sub.4 alkyl, C.sub.3 or C.sub.4 alkenyl, C.sub.3 alkynyl or C.sub.3 haloalkenyl are novel compounds.Type: GrantFiled: January 27, 1978Date of Patent: December 26, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Cynthia J. Mussinan, Braja D. Mookherjee, Manfred H. Vock, Frederick L. Schmitt, Edward J. Shuster, James M. Sanders, Bette M. Light, Edward J. Granda