Plural Oxygens Bonded Directly To The Same Carbon (e.g., Acetals, Ketals, Orthoesters, Orthocarbonates, Etc.) Patents (Class 568/591)
  • Patent number: 4272629
    Abstract: The invention relates to (1.alpha., 2.alpha., 4.alpha., 6.alpha.)-3-oxatricyclo[4.2.0.0.sup.2,4 ]octane-7-one and derivatives thereof in which the ketone group is protected, which compounds are useful intermediates in the preparation of natural and synthetic prostaglandins. Processes for the preparation of these compounds are described and exemplified as are processes for their conversion into known prostaglandin intermediates.
    Type: Grant
    Filed: July 23, 1979
    Date of Patent: June 9, 1981
    Assignee: Allen & Hanburys Limited
    Inventor: Stanley M. Roberts
  • Patent number: 4258207
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: March 24, 1981
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4258205
    Abstract: New 2,2-dimethylcyclopropanecarbaldehyde dimethyl acetal derivatives of the formula ##STR1## wherein X is --CH.sub.2 OC(O)CH.sub.3, --CH.sub.2 OH, or --CHO are useful chemical intermediates for the preparation of pesticidally active cyclopropanecarboxylates.
    Type: Grant
    Filed: December 4, 1978
    Date of Patent: March 24, 1981
    Assignee: Shell Oil Company
    Inventors: Johannes Van Berkel, Hendrik C. Kelderman
  • Patent number: 4241081
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl,--CHO,--C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: July 23, 1979
    Date of Patent: December 23, 1980
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4234512
    Abstract: 2-(2,2-Dimethoxyethyl-3,3-dimethylcyclopropanecarbaldehyde and 2-[2-(2,2-dihalovinyl)-3,3-dimethylcyclopropyl]ethanal dimethyl acetals are new pyrethroid intermediates. They are prepared from 2-(2-hydroxymethyl-3,3-dimethylcyclopropyl)ethanal dimethyl acetal.
    Type: Grant
    Filed: July 9, 1979
    Date of Patent: November 18, 1980
    Assignee: Shell Oil Company
    Inventors: Johannes Van Berkel, Hendrik C. Kelderman
  • Patent number: 4233464
    Abstract: 1-[3-Methyl-3,5,5-trialkoxy-pent-1-yn-1-yl]-2,6-dimethyl-cyclohex-1-enes, which may or may not be methyl-substituted in the 2- and/or 6-position, are obtained by reacting the corresponding 1-[3-methyl-but-1-yn-3-en-1-yl]-2,6-dimethyl-cyclohex-1-enes with orthoformic acid esters in the presence of acid condensing agents. The new compounds provide a new method of access to the compounds of carotinoid chemistry, especially to vitamin A, which avoids the conventional expensive synthesis via phosphorus ylide compounds.
    Type: Grant
    Filed: April 12, 1978
    Date of Patent: November 11, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Baumann, Werner Hoffmann
  • Patent number: 4230891
    Abstract: New 2-(2,2-dihalovinyl)-3,3-dimethylcyclopropane derivatives of the formula ##STR1## wherein each Hal is a halogen atom and R is dimethoxyethyl, 2-acetyl-3-oxobutyl, 2-methoxycarbonylpropyl or 2-acetyl-2-hydroxy-3-oxobutyl, are useful chemical intermediates for the preparation of pesticidally active cyclopropanecarboxylates.
    Type: Grant
    Filed: December 5, 1978
    Date of Patent: October 28, 1980
    Assignee: Shell Oil Company
    Inventors: Pieter A. Verbrugge, Petrus A. Kramer, Johannes Van Berkel, Hendrik C. Kelderman
  • Patent number: 4227022
    Abstract: A total synthesis of canthaxanthin or dinor-canthaxanthin, known food coloring agents, from pentols.
    Type: Grant
    Filed: October 10, 1978
    Date of Patent: October 7, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Michael Rosenberger
  • Patent number: 4222964
    Abstract: 2-(2,2-Dihalovinyl-3,3-dimethylcyclopropyl)ethanal is a new chemical compound and useful intermediate in the preparation of certain pyrethroid esters. It is prepared by hydrolysis of 2-[2-(2,2-dihalovinyl)-3,3-dimethylcyclopropyl]ethylidene diacetate, preferably in the presence of an acid.
    Type: Grant
    Filed: July 9, 1979
    Date of Patent: September 16, 1980
    Assignee: Shell Oil Company
    Inventors: Johannes Van Berkel, Johannes L. M. Syrier, Hendrik C. Kelderman
  • Patent number: 4209643
    Abstract: A process is described for the production of predominately linear and alpha-branched acetals by reacting a C.sub.3 or higher alpha or internal olefin, carbon monoxide, hydrogen, and a C.sub.1 -C.sub.5 alkanol using a cobalt catalyst in the presence of a promoter which is a quaternary ammonium salt such as N-benzyl,N,N,N-trimethylammonium methoxide. When a quaternary ammonium salt is used, an increase in the rate of reaction is effected.
    Type: Grant
    Filed: December 11, 1978
    Date of Patent: June 24, 1980
    Assignee: Ethyl Corporation
    Inventor: Kju H. Shin
  • Patent number: 4209642
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: June 24, 1980
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4209644
    Abstract: An unsaturated carbonyl compound, for example, one expressed by the following formula, ##STR1## is prepared by maintaining at an elevated temperature a novel allyl acetal of a .beta.,.gamma.-unsaturated aldehyde, for example, one expressed by the following formula ##STR2## The allyl acetal can be derived, for example, for 3-methyl-3-butenal-1 having 5 carbon atoms and prenyl alcohol having 5 carbon atoms. Thus, the unsaturated aldehyde having the increased number of carbon atoms can be formed in a high yield by a relatively simple reaction.
    Type: Grant
    Filed: November 30, 1977
    Date of Patent: June 24, 1980
    Assignee: Teijin Limited
    Inventors: Yataro Ichikawa, Teizo Yamaji, Mamoru Yamamoto
  • Patent number: 4206151
    Abstract: This disclosure describes novel 15-deoxy-16 hydroxy-16-substituted prostanoic acid analogs in which the C-1 carboxyl is replaced by a primary alcohol and carboxylic acid esters, carbonates and carbomates thereof. The prostanoic carbinols and carboxylic acid esters thereof described herein have utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.
    Type: Grant
    Filed: December 21, 1978
    Date of Patent: June 3, 1980
    Assignee: American Cyanamid Company
    Inventor: Charles V. Grudzinskas
  • Patent number: 4203811
    Abstract: p-Benzoquinone-diketals of the formual I ##STR1## in which R is H, (C.sub.1 -C.sub.4)-alkyl or halogen, and R.sup.1 is (C.sub.1 -C.sub.4)-alkyl, are prepared by anodic oxidation of benzene or an alkoxybenzene of the formulae ##STR2## in which R and R.sup.1 are as defined for formula I, in methanol containing less than about 5% by weight of water, in th presence of at least one alkali metal fluoride, ammonium fluoride and/or phosphonium fluoride as supporting electrolyte the pH being maintained below 7 by addition of HF.It is especially advantageous to carry out the anodic oxidation in a continuous-flow cell with the use of bipolar electrodes of glass-like carbon wherein the cathode surface is coated with a material reducing the hydrogen overvoltage, preferably titanium carbide.
    Type: Grant
    Filed: August 30, 1978
    Date of Patent: May 20, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Jurgen Cramer
  • Patent number: 4152355
    Abstract: A new intermediate of formula I ##STR1## in which X is chlorine, bromine or hydrogen and Y is a free or protected --CHO group, which is used in the manufacture of boll weevil sex pheromone components of formula II ##STR2## in which Z is --CHO or --CH.sub.2 OH, by catalytic hydrogenation, optionally with protection of the formyl group of II by acetalisation. Compound II is prepared by formylation of isophorone directly or after reduction and dehydration.
    Type: Grant
    Filed: February 3, 1977
    Date of Patent: May 1, 1979
    Assignee: Naarden International N.V.
    Inventor: Petrus C. Traas
  • Patent number: 4136124
    Abstract: Dialkyl-ketals are manufactured by reacting ketones with alkanols in the presence of an acid condensing agent and of an at least equivalent amount, based on the ketone, of anhydrous calcium sulfate.
    Type: Grant
    Filed: August 1, 1977
    Date of Patent: January 23, 1979
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Zinke-Allmang, Walter Scheidmeir
  • Patent number: 4133836
    Abstract: A process for the manufacture of acetals by reacting aliphatic aldehydes with aliphatic alcohols, especially olefinically unsaturated aldehydes and allyl alcohols, in the presence of a distillable acid, especially nitric acid, using a rectifying column as the reaction vessel. The products may be used as starting materials for plastics, active substances, scents and vitamins.
    Type: Grant
    Filed: May 31, 1977
    Date of Patent: January 9, 1979
    Assignee: BASF Aktiengesellschaft
    Inventors: Axel Nissen, Gerd Kaibel