Acyclic Polycarbon Hydrocarbyl Group Bonded Directly To The Benzene Group Patents (Class 568/766)
  • Patent number: 4297284
    Abstract: 2,3-Dihydro-2,2-dimethyl-7-hydroxybenzofuran is prepared by heating isobutenylpyrocatechol or isobutenylpyrocatechol/methallylpyrocatechol admixtures, at cyclization/isomerization temperatures, in the presence of a catalytic amount of an organic sulfonic acid.
    Type: Grant
    Filed: July 22, 1980
    Date of Patent: October 27, 1981
    Assignee: Rhone-Poulenc Agrochimie
    Inventor: Daniel Michelet
  • Patent number: 4284829
    Abstract: Compounds useful for pharmacological and medicinal purposes having the formulae ##STR1## wherein R is H, C.sub.1 -C.sub.5 alkanoyl; R.sub.1 is H, benzyl, C.sub.1 14 C.sub.5 alkanoyl, P(O)(OH).sub.2, --CO(CH.sub.2).sub.2 COOH or a basic acyl group; each of R.sub.2 and R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, phenyl, pyridyl or (CH.sub.2).sub.y C.sub.6 H.sub.5 ; y is 1-4; R.sub.3 is H or CH.sub.3 ; Z is C.sub.1 -C.sub.13 alkylene or --(alk.sub.1).sub.m --O--(alk.sub.2).sub.n --; each of (alk.sub.1) and (alk.sub.2) is C.sub.1 -C.sub.13 alkylene with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl, phenyl, fluorophenyl or chlorophenyl; intermediates therefor and methods for their preparation and use.
    Type: Grant
    Filed: December 22, 1978
    Date of Patent: August 18, 1981
    Assignee: Pfizer Inc.
    Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4283569
    Abstract: Compounds useful for pharmacological and medicinal purposes having the formulae ##STR1## wherein R is H, C.sub.1 -C.sub.5 alkanoyl; R.sub.1 is H, benzyl, C.sub.1 -C.sub.5 alkanoyl, P(O)(OH).sub.2, --CO(CH.sub.2).sub.2 COOH or a basic acyl group; each of R.sub.2 and R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, phenyl, pyridyl or (CH.sub.2).sub.y C.sub.6 H.sub.5 ; y is 1-4; R.sub.3 is H or CH.sub.3 ; Z is C.sub.1 -C.sub.13 alkylene or --(alk.sub.1).sub.m --O--(alk.sub.2).sub.n --; each of (alk.sub.1) and (alk.sub.2) is C.sub.1 -C.sub.13 alkylene with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl, phenyl, fluorophenyl or chlorophenyl; intermediates therefor and methods for their preparation and use.
    Type: Grant
    Filed: September 13, 1977
    Date of Patent: August 11, 1981
    Assignee: Pfizer Inc.
    Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4252985
    Abstract: The process relates to the preparation of o-methallyloxyphenol by the action of methallyl chloride on pyrocatechol in the presence of a basic agent.It consists in carrying out the reaction in a two-phase liquid reaction medium comprising water and a water-immiscible organic solvent, at a temperature between 50.degree. and 140.degree. C., in the presence of a catalyst chosen from amongst quaternary ammonium derivatives and phosphonium derivatives, using, as the basic agent, an alkali metal or alkaline earth metal hydroxide or an alkali metal carbonate or bicarbonate.It makes it possible to obtain the monoether selectively by minimizing the formation of diether and of alkylation products of the benzene nucleus of the pyrocatechol.
    Type: Grant
    Filed: June 18, 1979
    Date of Patent: February 24, 1981
    Assignee: Philagro
    Inventor: Michel Rakoutz
  • Patent number: 4229356
    Abstract: A process for producing hydro-precursors for vitamin K.sub.1 and vitamin K.sub.2 which comprises reacting (A) 2-methylhydronaphthoquinone-1,4 with (B) a compound selected from the group consisting of phytyl bromide, isophytyl bromide, geranyl bromide, farnesyl bromide, geranylgeranyl bromide and the corresponding chlorides in a reaction system which comprises an aqueous phase comprising an aqueous solution of an alkali and an oily phase comprising a hydrophobic organic solvent, in the presence of a salt comprising a quaternary ammonium ion or a tetraalkyl phosphonium ion represented by the formula (I) or formula (II): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each represent an alkyl or aralkyl group containing from 1 to 20 carbon atoms and the sum of the carbons in R.sub.1, R.sub.2, R.sub.3 and R.sub.4 groups is at least 12. The resultant hydro-precursor is oxidized to convert it into vitamin K.sub.1 or vitamin K.sub.2.
    Type: Grant
    Filed: February 27, 1979
    Date of Patent: October 21, 1980
    Assignee: Wakunaga Yakuhin Kabushiki Kaisha
    Inventors: Iwao Tabushi, Hiroyuki Sugimoto, Akira Yazaki
  • Patent number: 4226800
    Abstract: Phenolic materials containing propargyl groups are prepared by reacting a polyhydric, phenolic material with propargyl bromide, the reaction being conducted in an aqueous sodium hydroxide solution. The products can be thermally polymerized to polymers which are useful as adhesives and as matrix resins in the fabrication of composites.
    Type: Grant
    Filed: June 14, 1979
    Date of Patent: October 7, 1980
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventor: Lewellyn G. Picklesimer
  • Patent number: 4218368
    Abstract: Aromatic nitro compounds are disclosed where the aromatic ring contains electron-withdrawing groups and said aromatic nitro compound is capable of undergoing intramolecular nucleophilic displacement after reduction of the nitro group. The compounds are especially useful in photographic elements where an image dye-providing material or a photographic reagent are released upon cleavage from the compound.
    Type: Grant
    Filed: July 26, 1978
    Date of Patent: August 19, 1980
    Assignee: Eastman Kodak Company
    Inventors: Jerald C. Hinshaw, Richard P. Henzel
  • Patent number: 4209648
    Abstract: Alkylated hydroquinones are prepared by reacting hydroquinone with olefins having 8 and 9 carbon atoms.
    Type: Grant
    Filed: November 7, 1973
    Date of Patent: June 24, 1980
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Kirkwood S. Cottman
  • Patent number: 4207264
    Abstract: A continuous process for cleaving aralkyl hydroperoxides in acid media to yield phenols and carbonyl compounds in a reactor arranged and operated to limit the total residence time to less than the time required to form discoloration products.
    Type: Grant
    Filed: March 27, 1973
    Date of Patent: June 10, 1980
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: John E. Anderson, Ernest G. Hildenbrand
  • Patent number: 4201879
    Abstract: A process is disclosed for producing (S)-(+)-6-hydroxy-2,5,7,8-tetramethylchroman-2-methanol from either alkyl(R)-2-benzyloxy-3-hydroxy-2-methyl-propionate or (S)-2,2,4-trimethyl-1,3-dioxolan-4-ethanol including intermediates in this synthesis.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: May 6, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Barner, Max Schmid
  • Patent number: 4174460
    Abstract: A process for the hydroxylation of phenols and phenol ethers in the nucleus with hydrogen peroxide wherein a phenol or a phenol ether is reacted at the start of the reaction with substantially anhydrous hydrogen peroxide and wherein the reaction is carried out in the presence of a strong acid.
    Type: Grant
    Filed: March 31, 1977
    Date of Patent: November 13, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hermann Seifert, Helmut Waldman, Wulf Schwerdtel, Wolfgang Swodenk
  • Patent number: 4160113
    Abstract: The present invention is related to a process for the manufacture of resorcinols by catalytic dehydrogenation of cyclohexane diones-(1,3) in the liquid phase by means of a dehydrogenating mixture consisting of a solvent and of a catalyst containing a noble metal from Group VIII of the Periodic Table.
    Type: Grant
    Filed: November 11, 1977
    Date of Patent: July 3, 1979
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner H. Muller, Knut Riedel, Hans Krekeler
  • Patent number: 4139545
    Abstract: Novel compounds of the formulae ##STR1## wherein R represents lower alkyl or lower alkoxy, A represents --CH.sub.2 --, --CO-- or ##STR2## n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.
    Type: Grant
    Filed: April 30, 1975
    Date of Patent: February 13, 1979
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroshi Morimoto, Isuke Imada, Masazumi Watanabe, Mitsuru Kawada
  • Patent number: 4138411
    Abstract: Aromatic alkenyl compounds, for example, eugenol and safrole, are isomerized, for example to isoeugenol and isosafrole, by contact with a ruthenium or osmium catalyst.
    Type: Grant
    Filed: April 14, 1976
    Date of Patent: February 6, 1979
    Assignee: Rhone-Poulenc S. A.
    Inventor: Pierre Gandilhon
  • Patent number: 4108909
    Abstract: A method for the production of n-alkylated cresylic acids such as n-hexyl resorcinol by direct alkylation of a cresylic acid such as resorcinol under liquid phase conditions.
    Type: Grant
    Filed: November 18, 1976
    Date of Patent: August 22, 1978
    Assignee: Continental Oil Company
    Inventors: Bruce Eugene Leach, Charles M. Starks
  • Patent number: 4101591
    Abstract: Haloloweralkyl ethynylbenzene compounds and their derivatives which are useful for the treatment for the relief of inflammation, pain and fever.
    Type: Grant
    Filed: November 23, 1976
    Date of Patent: July 18, 1978
    Assignee: William H. Rorer, Inc.
    Inventor: Julius Diamond
  • Patent number: 4093667
    Abstract: Preparation of 4-n-hexylresorcinol is achieved by a two-step process involving: first preparing hexyl resorcyl ethers by reacting resorcinol with a hexylating agent having the general formula 1-C.sub.6 H.sub.13 X in the presence of a base, and second, treating the reaction product obtained with a catalyst to yield 4-n-hexylresorcinol by a rearrangement process. X can be selected from the group consisting of Cl- Br-, I-, ArSO.sub.3.sup.-, and similar materials.
    Type: Grant
    Filed: March 14, 1977
    Date of Patent: June 6, 1978
    Assignee: Continental Oil Company
    Inventor: Charles Masterson Starks
  • Patent number: 4087410
    Abstract: 2,6-Dimethoxyphenol reacts with a tertiary carbinol in the presence of an acid to provide exclusively a 1-hydroxy-2,6-dimethoxy-4-tertiary alkyl)benzene, which when reacted with a halogenated disubstituted phosphite affords a 2,6-dimethoxy-4-tertiary alkyl)phenyl disubstituted phosphate. Reduction of the phenyl phosphate derivative by reaction with an alkali metal affords a 1-(tertiary alkyl)-3,5-dimethoxybenzene, which upon reaction with a demethylating agent provides a 5-(tertiary alkyl)resorcinol.
    Type: Grant
    Filed: June 14, 1976
    Date of Patent: May 2, 1978
    Assignee: Eli Lilly and Company
    Inventors: Samuel J. Dominianni, Charles W. Ryan