The Hydroxy Is Attached Indirectly To The Ring Patents (Class 568/826)
  • Patent number: 5202503
    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: November 12, 1991
    Date of Patent: April 13, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Wolf, Hans Theobald, Norbert Goetz
  • Patent number: 5187286
    Type: Grant
    Filed: March 25, 1991
    Date of Patent: February 16, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt
  • Patent number: 5153229
    Abstract: A process for producing a stable, bactericidal and fungicidal composition which consists essentially of bubbling air or oxygen into limonene, to produce an oxidized limonene having a rapid bactericidal activity as evidenced by the capability of killing at least 99.99% of the bacteria in a suitable culture medium inoculated with 10.sup.6 colony forming units of Staphylococcus aureus ATCC 25923 per ml.
    Type: Grant
    Filed: June 1, 1990
    Date of Patent: October 6, 1992
    Assignee: Doyle E. Chastain
    Inventors: Doyle E. Chastain, W. Eugene Sanders, Jr., Christine C. Sanders
  • Patent number: 5132471
    Abstract: .alpha.-Bisabolol is purified by distilling a plant extract containing .alpha.-bisabolol under reduced pressure and drawing off the purified .alpha.-bisabolol in the lower half of a distillation column as side product, and feeding in the extract above the side outlet.
    Type: Grant
    Filed: April 24, 1991
    Date of Patent: July 21, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerald Lauterbach, Otto Hertel, Klaus Euler
  • Patent number: 4999454
    Abstract: The invention is directed to a new process for the preparation of carbinols of the general formula I ##STR1## by reaction chloral and olefins of the general formula ##STR2## and by optional acylation of the product comprising dissolving a catalyst of the general formula IIIFe.sub.n (NH.sub.4).sub.x Y.sub.m .multidot.A.sub.p IIIin chloral, then adding the olefin of the general formula II in order to produce a complex of the general formula IV ##STR3## from which a complex of the general formula V ##STR4## is formed, and from the reaction mixture a compound of the general formula I is obtained whereafter(a) the residual complex of the general formula V dissolved in the product is decomposed with an acidic solution and if desired the obtained product is distilled or(b) the product in the reaction mixture is acylated.The compounds prepared according to the invention can be utilized as intermediates when preparing e.g., permethrin and other pyrethroid insecticides.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: March 12, 1991
    Assignee: Chinoin Gyogyszer ES Vegyeszeti Termekek Gyara RT.
    Inventors: Rudolf Soos, Jozsef Nemes, Miklos Szelestei, Istvan Schler, Laszlo Vidra, Istvan Szekely
  • Patent number: 4920096
    Abstract: High quality cedar wood oil is recovered from raw cedar wood with substantially improved efficiency employing the solvent extraction method of this invention. By submerging cedar wood pulp or sawdust in a suitable water insoluble solvent for a predefined time period, a purified cedar wood oil extract is easily attained after filtration of the cedar wood pulp and distillation removal of the solvent. Furthermore, depending upon the end use or operating system, the solvent extraction method of this invention may be conducted as either a batch process or a continuous process.
    Type: Grant
    Filed: October 6, 1988
    Date of Patent: April 24, 1990
    Inventor: Paul Z. Bedoukian
  • Patent number: 4892941
    Abstract: Disclosed are tetraphenyl porphyrins which are beta-substituted by fluoro or chloro and/or bear electronegative substituents on the phenyl including one or two water solubilizing substituents. The new porphorins are particularly suitable as catalysts in a variety of oxidative reactions and methods.
    Type: Grant
    Filed: April 15, 1988
    Date of Patent: January 9, 1990
    Inventors: David H. Dolphin, Taku Nakano, Thomas K. Kirk, Tilak P. Wijesekera, Roberta L. Farrell, Theodore E. Maione
  • Patent number: 4868339
    Abstract: Multimethyl cyclohexene or cyclohexane derivatives having woody, spicy, amber or violet odors are disclosed. The derivatives can be formulated into perfurmes, talcs, lotions, cremes and air fresheners.
    Type: Grant
    Filed: September 23, 1987
    Date of Patent: September 19, 1989
    Assignee: BASF K & F Corporation
    Inventors: Philip A. Christenson, Brian J. Drake
  • Patent number: 4710316
    Abstract: Compounds of the general formula (I) ##STR1## and compounds of the general formula (II) ##STR2## in which R.sup.1 represents --OH, --CH.sub.2 OH, --CH.sub.2 --OCH.sub.3, --CHOH--CH.sub.3, --CHO or --CH(OCH.sub.3).sub.2,R.sup.2 represents methyl or ethyl,R.sup.3 represents hydrogen or methyl, andX represents hydrogen or methyl, are disclosed.Processes for the manufacture of certain compounds of formula (I) and for those of formula (II) are also provided. The compounds are useful as perfume materials.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: December 1, 1987
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Walter Hafner, Peter Ritter, Helmut Gebauer, Marlies Regiert
  • Patent number: 4704477
    Abstract: Compounds of the general formula ##STR1## wherein A is the ##STR2## group and in which R.sup.1 stands for hydrogen, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy and isopropoxy and R.sup.2 and R.sup.3 are hydrogen, methyl and ethyl. The compounds are used as perfume substances.
    Type: Grant
    Filed: March 7, 1986
    Date of Patent: November 3, 1987
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Helmut Gebauer, Hans Mehlin, Marlies Regiert
  • Patent number: 4638103
    Abstract: A method of preparing delta-terpineol by reacting 1,8-cineole with an alkali metal aryl compound resulting in an E2 elimination reaction of 1,8-cineole.
    Type: Grant
    Filed: October 1, 1985
    Date of Patent: January 20, 1987
    Assignee: Union Camp Corporation
    Inventor: Peter W. D. Mitchell
  • Patent number: 4638104
    Abstract: A method of preparing terpinen-4-ols and intermediates thereof, by reacting 1,4-cineole with an alkali metal aryl compound, resulting in an E2 elimination reaction of 1,4-cineole.
    Type: Grant
    Filed: October 1, 1985
    Date of Patent: January 20, 1987
    Assignee: Union Camp Corporation
    Inventor: Peter W. D. Mitchell
  • 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: 4609491
    Abstract: Novel odorant substances of the formula: ##STR1## wherein: one of the three dotted lines represents an optional bond,R.sup.1 represents hydrogen, an alkyl group of one to four carbons or an alkenyl group of two to four carbons,R.sup.2 represents hydrogen or methyl,R.sup.3 represents hydrogen or methyl, provided thatR.sup.2 and R.sup.3 are never both hydrogen, and novel fragrance compositions containing same.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: September 2, 1986
    Assignee: Givaudan Corporation
    Inventor: Hanspeter Schenk
  • Patent number: 4543431
    Abstract: Polyunsaturated ketones of formula ##STR1## having a double bond in position 2' or 3' of the side chain and possessing either an isolated double bond in position 1 or 2, or two conjugated double bonds in positions 1 and 3 of the ring, as indicated by the dotted lines, andwhereinindex n stands for integer 1 or 2, andeach of the symbols R.sup.1 to R.sup.7, identical or different, designates a hydrogen atom or a lower radical,are prepared by a process which makes use of tertiary diallyl carbinols as starting materials.
    Type: Grant
    Filed: February 14, 1984
    Date of Patent: September 24, 1985
    Assignee: Firmenich SA
    Inventors: Karl H. Schulte-elte, Roger L. Snowden, Bernard L. Muller
  • Patent number: 4487972
    Abstract: This specification discloses a process for the production of oxygenated compounds, more specifically aldehydes and alcohols, by reacting an olefin with hydrogen and carbon monoxide in the presence of, as a ctalyst, an insoluble polymer containing a functional group, which may be an amine, thiol, phosphine, or arsine group, having chemically bonded thereto a metal of Group VIII of the Periodic Table. The metal can be, for example, rhodium, cobalt, or ruthenium. The olefin can contain more than one carbon-to-carbon double bond, may be an open chain or a cyclic olefin, and may be substituted. Further, the olefin may be contained in a refinery stream such as a cracked gasoline. The reaction may be carried out in the presence of a polar solvent.
    Type: Grant
    Filed: April 22, 1980
    Date of Patent: December 11, 1984
    Assignee: Mobil Oil Corporation
    Inventors: Werner O. Haag, Darrell D. Whitehurst
  • Patent number: 4392993
    Abstract: New alicyclic unsaturated compounds useful as perfume ingredients and perfume compositions containing same. The new compounds have formula ##STR1## possessing a methyl group attached to the carbon atom at position 3 or 4 of the ring and one double bond in one of the positions of the carbonyl side chain as indicated by the dotted line.
    Type: Grant
    Filed: July 23, 1981
    Date of Patent: July 12, 1983
    Assignee: Firmenich, SA
    Inventors: Alan F. Thomas, Ferdinand Naf
  • Patent number: 4348543
    Abstract: The present invention describes cycloaliphatic alcohols prepared via a Diels-Alder reaction.
    Type: Grant
    Filed: February 12, 1981
    Date of Patent: September 7, 1982
    Assignee: Henkel Corporation
    Inventor: Edgar R. Rogier
  • Patent number: 4301018
    Abstract: Described are cyclohexenemethanols and uses thereof in augmenting or enhancing the aroma of fabric softener articles.
    Type: Grant
    Filed: January 18, 1980
    Date of Patent: November 17, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4301309
    Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as lower alkyl esters of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff, medicinal product and tobacco flavors. The cyclohexenemethanols are useful as precursors for the oxabicyclooctanes and are, themselves, useful for their organoleptic properties in perfumery and flavors as are the esters of said cyclohexenemethanols.
    Type: Grant
    Filed: November 16, 1979
    Date of Patent: November 17, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4283576
    Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as lower alkyl esters of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff and medicinal product flavors. The cyclohexenemethanols are useful as precursors for the oxabicyclooctanes.
    Type: Grant
    Filed: December 5, 1979
    Date of Patent: August 11, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4263208
    Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as lower alkyl esters of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff, medicinal product and tobacco flavors. The cyclohexenemethanols are useful as precursors for the oxabicyclooctanes and are, themselves, useful for their organoleptic properties in perfumery and flavors as are the esters of said cyclohexenemethanols.
    Type: Grant
    Filed: November 16, 1979
    Date of Patent: April 21, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4250342
    Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as organometallic salts of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff and medicinal product flavors. The cyclohexenemethanols and their organometallic salts are useful as precursors for the oxabicyclooctanes.
    Type: Grant
    Filed: November 16, 1979
    Date of Patent: February 10, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4250049
    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 to a solid or liquid anionic, cationic or nonionic detergent base from 0.005% up to 5% by weight of at least one compound defined according to the generic structure: ##STR1## wherein one of R.sub.1, R.sub.2 or R.sub.3 is methyl and the other two of R.sub.1, R.sub.2 and R.sub.3 is hydrogen; wherein the dashed line represents a carbon-carbon double bond or a carbon-carbon single bond with the proviso that when R.sub.1 is hydrogen, the dashed line represents a carbon-carbon double bond.
    Type: Grant
    Filed: February 8, 1980
    Date of Patent: February 10, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard A. Wilson, William L. Schreiber, Braja D. Mookherjee, Jacob Kiwala, Joaquin F. Vinals, Manfred H. Vock, Gilbert Stork, Frederick L. Schmitt
  • Patent number: 4250118
    Abstract: An improved process for the preparation of cyclohexanone from benzene. Benzene is hydrogenated in a gaseous phase in a hydrogenation zone to form cyclohexane; cyclohexane is oxidized in a liquid phase to form a mixture containing cyclohexanol and cyclohexanone; and cyclohexanone is separated from this mixture and is catalytically dehydrogenated to form cyclohexanone and a hydrogen containing gas. The resulting hydrogen containing gas is introduced into a washing zone wherein it is washed with cyclohexane or benzene and the hydrogen gas thus purified is fed into the hydrogenation zone.
    Type: Grant
    Filed: April 20, 1979
    Date of Patent: February 10, 1981
    Assignee: Stamicarbon, B.V.
    Inventors: Theodorus J. van de Mond, Hubertus J. A. Delahaye
  • Patent number: 4243823
    Abstract: Processes and compositions are described for use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, smoking tobacco flavor and aroma and perfume and perfumed article aroma augmenting, enhancing and imparting compositions; and as foodstuff, chewing gum, toothpaste, medicinal product, smoking tobacco, perfume and perfumed article aroma and/or flavor imparting materials of 2,6,6-trimethyl-.alpha.-(iso)propenyl-1-cyclohexene-1-methanol and -1,3-cyclohexadiene-1-methanol derivatives or one or more of their geometric or stereoisomers as defined by the generic structure: ##STR1## wherein one of R.sub.1, R.sub.2 or R.sub.3 is methyl and the other two of R.sub.1, R.sub.2 and R.sub.3 represents hydrogen; the dashed line is a carbon-carbon double bond or a carbon-carbon single bond; with the proviso that when R.sub.1 is hydrogen, the dashed line is a carbon-carbon double bond.Addition of one or more of the 2,6,6-trimethyl-.alpha.
    Type: Grant
    Filed: May 15, 1979
    Date of Patent: January 6, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard A. Wilson, William L. Schreiber, Braja D. Mookherjee, Jacob Kiwala, Joaquin F. Vinals, Manfred H. Vock, Gilbert Stork, Frederick L. Schmitt
  • Patent number: 4222941
    Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as organometallic salts of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff and medicinal product flavors. The cyclohexenemethanols and their oganometallic salts are useful as precursors for the oxabicyclooctanes.
    Type: Grant
    Filed: June 15, 1979
    Date of Patent: September 16, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4221721
    Abstract: Described are cyclic chemical compounds useful for their organoleptic properties in flavors, fragrances, colognes, perfumed articles and smoking tobaccos defined according to the structure: ##STR1## wherein R.sub.1 is hydrogen or methyl and R.sub.2 is C.sub.4 or C.sub.5 alkyl or C.sub.
    Type: Grant
    Filed: June 27, 1979
    Date of Patent: September 9, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4217252
    Abstract: Described is a process for augmenting or enhancing the aroma of a perfume composition as well as perfume and cologne compositions containing a mixture consisting essentially of compounds having the structures: ##STR1## and wherein the mixture contains 30% of the compounds having the structures; ##STR2## and 60% of the compound having the structure: ##STR3##
    Type: Grant
    Filed: May 15, 1979
    Date of Patent: August 12, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Robert W. Trenkle, Braja D. Mookherjee, Robin Kasper, Manfred H. Vock, Joaquin Vinals, Jacob Kiwala, Frederick L. Schmitt
  • Patent number: 4215230
    Abstract: Ionones and irones are produced by thermal rearrangement of novel propargylic alcohols, as follows: ##STR1## wherein R.sup.1 is a lower alkyl group, R.sup.2 is hydrogen or methyl and the dotted lines in the product formula reflect the existence of a double bond at either one or the other of the positions indicated.
    Type: Grant
    Filed: May 23, 1978
    Date of Patent: July 29, 1980
    Assignee: Kuraray Co., Ltd.
    Inventors: Takashi Ohnishi, Yoshiji Fujita, Michihiro Ishiguro, Takashi Nishida
  • Patent number: 4197328
    Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as lower alkyl esters of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff and medicinal product flavors. The cyclohexenemethanols are useful as precursors for the oxabicyclooctanes.
    Type: Grant
    Filed: February 2, 1979
    Date of Patent: April 8, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4195100
    Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexenemethanols as well as organometallic salts of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff and medicinal product flavors. The cyclohexenemethanols and their organometallic salts are useful as precursors for the oxabicyclooctanes.
    Type: Grant
    Filed: February 16, 1979
    Date of Patent: March 25, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4195099
    Abstract: Described are derivatives of 2-oxabicyclo[2.2.2]octanes and precursors therefor, cyclohexemethanols as well as lower alkyl esters of said cyclohexenemethanols. The oxabicyclooctanes are useful in perfumery and foodstuff, medicinal product and tobacco flavors. The cyclohexenemethanols are useful as precursors for the oxabicyclooctanes and are, themselves, useful for their organoleptic properties in perfumery and flavors as are the esters of said cyclohexenemethanols.
    Type: Grant
    Filed: October 20, 1978
    Date of Patent: March 25, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4172850
    Abstract: Described is a process for preparing several 1-acyl-2,6,6-trimethylcyclohexene derivatives defined by the generic structure: ##STR1## wherein R.sub.1 is hydrogen or ethylidene having the structure:[H.sub.3 C--C.dbd. ;R.sub.2 is hydrogen or no group; one of the wavy lines is a carbon-carbon double bond and the other of the wavy lines is a carbon-carbon single bond; with the proviso that when the .DELTA..sup.2,3 bond (as shown by the wavy line between the "2" and the "3" position of the ring) is a carbon-carbon double bond, then R.sub.2 is hydrogen and R.sub.
    Type: Grant
    Filed: December 1, 1978
    Date of Patent: October 30, 1979
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Robert W. Trenkle, Braja D. Mookherjee, Robin Kasper, Manfred H. Vock, Joaquin Vinals, Jacob Kiwala, Frederick L. Schmitt
  • Patent number: 4140690
    Abstract: Terpenes are oxidized by contacting the terpene and oxygen with a catalyst. The catalyst may be either (a) a bismuth molybdate or (b) antimony oxide containing iron oxide and/or uranium oxide.
    Type: Grant
    Filed: April 22, 1977
    Date of Patent: February 20, 1979
    Assignee: The Standard Oil Company
    Inventors: Serge R. Dolhyj, Louis J. Velenyi
  • Patent number: 4125484
    Abstract: Novel tertiary alcohols of the general formula: ##STR1## in which R.sub.1 represents an alkenyl or a cycloalkyl or cycloalkenyl optionally substituted by one or more alkyl groups, R.sub.2 represents hydrogen or alkyl; or R.sub.1 and R.sub.2, together with the carbon atom to which they are linked, from a bicyclo group optionally substituted by up to two alkyl groups; R.sub.3 and R.sub.4 each represents an alkyl group, and Y represents a divalent aliphatic group of up to 4 carbon atoms, are disclosed along with their use as aroma chemicals and a process for their preparation.
    Type: Grant
    Filed: February 24, 1977
    Date of Patent: November 14, 1978
    Assignee: Shell Oil Company
    Inventors: Robin T. Gray, Aaldert J. De Jong
  • Patent number: 4113968
    Abstract: When 1-halogeno-3-alkene-2-ol is reacted with an ortho-carboxylic ester and/or a ketene acetal, a .gamma.-halogeno-.delta.-unsaturated-carboxylic ester is obtained as a main reaction product. When this intermediate is treated with a basic substance, a substituted cyclopropane-carboxylic ester is formed. This ester can be used as an insecticide or an agricultural chemical as it is or after the alcohol residue of the ester has been converted to other alcohol residue.
    Type: Grant
    Filed: September 26, 1975
    Date of Patent: September 12, 1978
    Assignee: Kuraray Co., Ltd.
    Inventors: Fumio Mori, Yoshiaki Omura, Takashi Nishida, Kazuo Itoi