Ether Oxygen Is Ortho To The Hydroxy Patents (Class 568/652)
  • Patent number: 5015769
    Abstract: New 3-amino-4-nitrophenols, the process for preparation thereof and their use in dyeing keratinous fibers, and new intermediate 4,5-dinitrophenols.The present invention relates to a 3-amino-4-nitrophenol of formula: ##STR1## where Z denotes --CH.sub.2 --W, W denoting hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl, (C.sub.1 -C.sub.3)alkoxy(C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.3)hydroxyalkoxy(C.sub.1 -C.sub.6)alkyl and R denotes hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl or (C.sub.1 -C.sub.3)alkoxy(C.sub.1 -C.sub.6)alkyl, the process for preparation thereof and the intermediate compound of formula: ##STR2## in which Z' denotes CH.sub.2 --W, W denoting C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.6 polyhydroxyalkyl, (C.sub.1 -C.sub.3)alkoxy-(C.sub.1 -C.sub.6)alkyl or (C.sub.1 -C.sub.3)hydroxyalcoxy(C.sub.1 -C.sub.6)alkyl.
    Type: Grant
    Filed: June 19, 1990
    Date of Patent: May 14, 1991
    Assignee: L'Oreal
    Inventors: Alex Junino, Gerard Lang, Alain Genet
  • Patent number: 4982012
    Abstract: 2-Methallyloxyphenol is produced selectively in good yield, high purity and without having to separate and recycle large amounts of catechol, in the reaction of methallyl chloride with catechol, by forming a substantially non-aqueous mixture of an alkali metal catecholate and a molar excess of methallyl chloride perferably in a polar organic solvent in which the methallyl chloride is substantially insoluble, agitating the mixture to produce a two-phase system comprising an organic first phase containing product 2-methallyloxyphenol dissolved in methallyl chloride and a polar second phase containing unreacted catecholate, and recovering product 2-methallyloxyphenol from the first plase. The presence of a quaternary ammonium or phosphonium catalyst in the reaction mixture further reduces undesired ring-alkylated by-products.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: January 1, 1991
    Assignee: FMC Corporation
    Inventor: John W. Ager, Jr.
  • Patent number: 4959391
    Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.
    Type: Grant
    Filed: July 14, 1988
    Date of Patent: September 25, 1990
    Assignee: Gruenenthal GmbH
    Inventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin O. Kiesewetter, Ulrich G. P. Seippl
  • Patent number: 4946865
    Abstract: A compound of the formula: ##STR1## wherein X is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.3 alkyl group or a C.sub.1 -C.sub.3 alkoxy group and Y is a hydrogen atom, a halogen atom, a cyano group, a formyl group, an ethylene-dioxymethyl group, a hydroxyl group, a hydroxymethyl group or a group of either one of the formulas: --CH.dbd.N--OR.sup.1, --COOR.sup.2, --CONH--R.sup.2 and --CH(OR.sup.3).sub.2 in which R.sup.1 is a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.5 alkenyl group, a C.sub.3 -C.sub.5 alkynyl group, a halo(C.sub.3 -C.sub.5)alkynyl group or a C.sub.1 -C.sub.3 alkyl group substituted with a phenyl group or a cyano group, R.sup.2 is a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.5 alkenyl group or a C.sub.3 -C.sub.5 alkynyl group and R.sup.3 is a C.sub.1 -C.sub.
    Type: Grant
    Filed: December 24, 1986
    Date of Patent: August 7, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junya Takahashi, Shigeko Nakamura
  • Patent number: 4851587
    Abstract: 2-Methallyloxyphenol precursor to 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran is prepared selectively and in good yield in the etherification of an alkali metal catecholate by methallyl chloride in an improved process using the same solvent medium for both the precursor and the hydroxybenzofuran, the process characterized by a solvent medium comprising an aromatic hydrocarbon solvent, the medium also containing an amine selected from alkylamines and N-heterocyclic amines. The amine forms a quaternary salt with the methallyl chloride in situ to catalyze the etherification and the aromatic solvent permits rearrangement of the product and Claisen closure to a benzofuran intermediate without solvent exchange.
    Type: Grant
    Filed: May 31, 1988
    Date of Patent: July 25, 1989
    Assignee: FMC Corporation
    Inventors: Borivoj Franko-Filipasic, James Snyder
  • Patent number: 4820879
    Abstract: The present invention provides a process for making hydrocarbyloxy magnesium halides by reacting in an inert atmosphere under anhydrous conditions activated magnesium metal with an oxygen containing compound of 1 to 20 carbon atoms and an anhydrous hydrogen halide to produce a hydrocarbyloxy magnesium halide.
    Type: Grant
    Filed: June 5, 1987
    Date of Patent: April 11, 1989
    Assignee: Lithium Corporation of America
    Inventor: Vijay C. Mehta
  • Patent number: 4760087
    Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.
    Type: Grant
    Filed: May 13, 1986
    Date of Patent: July 26, 1988
    Assignee: Gruenenthal GmbH
    Inventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin Kiesewetter, Ulrich G. P. Seipp
  • Patent number: 4657700
    Abstract: The invention concerns novel fragrance compositions containing benzyl ethers of the formula ##STR1## wherein: R.sup.1 represents an alkyl group containing one to three carbon atoms, and,R.sup.2 represents hydrogen or an alkanoyl group containing one to four carbon atoms.Novel benzyl ethers of formula I also form part of the present invention.
    Type: Grant
    Filed: September 21, 1984
    Date of Patent: April 14, 1987
    Assignee: Givaudan Corporation
    Inventor: Paul A. Ochsner
  • Patent number: 4644085
    Abstract: The invention relates to a new anti-cancer chemical compound which has been called rooperol and certain derivatives thereof of the general formula ##STR1## in which A is chosen from the group including a phenyl group, a substituted phenyl group and --CH.sub.2 --O--R.sup.5 where R.sup.5 =H, an alkyl (C.sub.1 -C.sub.5), aralkyl or acyl substituent; R.sup.1 and R.sup.2 are chosen from substituents including H for both or singly if one of them is --OH, --NH.sub.2, --SH, ##STR2## or taken together R.sup.1 and R.sup.2 are =0; R.sup.3 is H or ##STR3## where R.sup.6 is an alkyl group (C.sub.1 -C.sub.7); either of R.sup.4 or B are chosen from substituents including H, ##STR4## a phenyl group, substituted phenyl group or a furyl group.
    Type: Grant
    Filed: June 4, 1985
    Date of Patent: February 17, 1987
    Assignee: Rooperol (NA) NV
    Inventors: Siegfried Drewes, Roelof W. Liebenberg
  • Patent number: 4639536
    Abstract: 2,3-Dihydro-2,2-dimethyl-7-hydroxybenzofuran is prepared by reacting catechol with isobutylene oxide or with a compound having the general formula ##STR1## wherein R is halogen or hydroxyl, and X is halogen, in the presence of a base to form the intermediate 2-(2-hydroxy-2-methylpropoxy) phenol and then thermally dehydrating, rearranging and cyclizing the resulting intermediate phenol in the presence of an acid catalyst to form 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran.
    Type: Grant
    Filed: August 30, 1984
    Date of Patent: January 27, 1987
    Assignee: Union Carbide Corporation
    Inventors: Constance A. Fellows, Wallace Y. Fu
  • Patent number: 4618627
    Abstract: A catechol derivative represented by the formula ##STR1## The compounds of this invention are useful for the prophylaxis and treatment for various allergic diseases, ischemic heart diseases and inflammations caused by slow reacting substance of anaphylaxis (SRS-A), since the compounds inhibit very potently the formation and release of SRS-A.
    Type: Grant
    Filed: May 11, 1984
    Date of Patent: October 21, 1986
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kiyoshi Murase, Toshiyasu Mase, Hideki Arima, Kenichi Tomioka
  • Patent number: 4618728
    Abstract: A method is disclosed for facilitating selective etherification of catechol with methallyl chloride in the absence of an etherification catalyst, in which there is employed a solvent system comprising an aliphatic ketone and an etherification aiding amount of water.
    Type: Grant
    Filed: February 22, 1985
    Date of Patent: October 21, 1986
    Assignee: FMC Corporation
    Inventors: Philip B. Hobson, Robert E. Keay
  • Patent number: 4599461
    Abstract: A process for preparing o-isopropoxyphenol (I) by means of the reaction: ##STR1## in which X is a halogen atom and in which the pyrocatechol (II) is reacted with the isopropyl halide (III) in the presence of an alkaline base in the solid state and of a solid-liquid phase transfer catalyst, in a reaction medium constituted by one or more organic solvents.The catalyst is constituted by a quaternary ammonium or phosphonium salt.The reaction is conducted in a nitrogen atmosphere, at atmospheric pressure, under agitation, at a temperature of preferably between 50.degree. C. and 130.degree. C.
    Type: Grant
    Filed: January 10, 1985
    Date of Patent: July 8, 1986
    Assignee: Brichima Spa
    Inventors: Paolo Maggioni, Francesco Minisci, Mariano Correale
  • Patent number: 4588835
    Abstract: A process for preparing an alkoxyphenol represented by the formula: ##STR1## wherein R is hydrogen, alkyl having 1 to 4 carbon atoms, formyl, hydroxymethyl, alkoxymethyl, dialkoxymethyl, acetoxymethyl or diacetoxymethyl, R' is alkyl having 1 to 4 carbon atoms, and n is an integer of 1 to 5, characterized in that a phenol halide represented by the formula: ##STR2## wherein R and n are as defined above, and X is chlorine or bromine is reacted, in the presence of a copper salt serving as a catalyst and of a solvent, with a product prepared by heating, in the presence of a dehydrating agent, an alkali metal hydroxide and a compound of the formula R'OH wherein R' is as defined above.
    Type: Grant
    Filed: October 19, 1984
    Date of Patent: May 13, 1986
    Assignee: Otsuka Kagaku Yakuhin Kabushiki Kaisha
    Inventors: Sigeru Torii, Hideo Tanaka, Mitsuo Akada
  • Patent number: 4542229
    Abstract: A process is described for preparing 2,3-dihydro-2,2-dimethylbenzofuran-7-ol (I), which is a useful intermediary in the preparation of Carbofuran, a known multi-functional insecticide.The process consists essentially of reacting the pyrocatechol and a methallylhalide in an inert organic solvent in the presence of a solid inorganic base and a suitable catalyst, to obtain o.methallyloxyphenol with high conversion and high selectivity; this product is thermally transposed to o.methallylpyrocatechol, which is finally cyclized to the product (I) by heterogeneous catalysis in the presence of solid acid catalysts.All stages of the process can be carried out in a single reaction medium, without separating intermediate products.
    Type: Grant
    Filed: April 11, 1983
    Date of Patent: September 17, 1985
    Assignee: Brichima S.p.A.
    Inventors: Paolo Maggioni, Francesco Minisci, Mariano Correale
  • Patent number: 4513109
    Abstract: The invention relates to phenols which contain a number of aromatic nuclei and in which the bridge formation of these nuclei is in the meta-position to the OH groups. These phenols have the formula I, wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined in claim 1.The novel phenols are most suitable for use as stabilizers for organic polymers and lubricants and have particularly good color properties.
    Type: Grant
    Filed: January 27, 1984
    Date of Patent: April 23, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Siegfried Rosenberger
  • Patent number: 4501910
    Abstract: The invention concerns a process transforming an aldehyde into a corresponding alkene, of the type wherein the aldehyde is placed in the presence of a phosphoric reagent and a base in an organic solvent.The process consists in using an alcohol as the solvent and as a base a mineral base which in an aqueous medium evinces a basic strength equal to or less than that of the hydroxide ion, or a strongly basic organic base of the amine family, and in limiting the hydration rate of the reaction medium to a value at most of 10 moles of water per mole of aldehyde.
    Type: Grant
    Filed: October 12, 1982
    Date of Patent: February 26, 1985
    Assignee: Agrifurane, S.A.
    Inventors: Michel Delmas, Antoine Gaset, Yves le Bigot
  • Patent number: 4487975
    Abstract: Phenols, including the polyhydric phenols, are selectively monoetherified with an alkyl or alkenyl carboxylate, or admixture of compounds adapted to in situ form such carboxylate, in the presence of a salt of a carboxylic acid.
    Type: Grant
    Filed: August 11, 1982
    Date of Patent: December 11, 1984
    Assignee: Rhone-Poulenc Industries
    Inventor: Serge Ratton
  • Patent number: 4465867
    Abstract: A process for preparing o-methallyloxyphenol by reacting catechol with methallyl chloride in the presence of at least one of KI and NaI serving as a catalyst with use of a base, and an organic solvent or a mixture of an organic solvent and water, the process being characterized in that methallyl chloride is reacted with the catalyst after the reaction to recover the catalyst as converted to methallyl iodide and reuse the catalyst.
    Type: Grant
    Filed: June 11, 1982
    Date of Patent: August 14, 1984
    Assignee: Otsuka Kagaku Yakuhin Kabushiki Kaisha
    Inventors: Tsukasa Maekawa, Takeshi Gondo, Shigeo Takahashi, Hidetoshi Kume
  • Patent number: 4465868
    Abstract: A process for preparing o-methallyloxyphenol characterized in that catechol and methallyl chloride are reacted with use of:A. at least one base selected from among carbonates and bicarbonates of alkali metals, bicarbonates of alkaline earth metals and amines at least 10 in pKa,B. at least one catalyst selected from among iodides of alkali metals or alkaline earth metals, hydrogen iodide and methallyl iodide, andC. a ketone solvent or ketone-water mixture solvent.
    Type: Grant
    Filed: June 11, 1982
    Date of Patent: August 14, 1984
    Assignee: Otsuka Kagaku Yakuhin Kabushiki Kaisha
    Inventors: Tsukasa Maekawa, Takeshi Gondo, Syozo Hayase
  • Patent number: 4420642
    Abstract: A process is disclosed for selectively removing catechol from a mixture comprising catechol, 2-methallyloxyphenol, various salts, and by-products by treating the mixture with aqueous base, the aqueous phase being preferably saturated with respect to salts present; the catechol may then be recovered for recycle by acidifying the resulting aqueous phase and extracting the acidified aqueous phase with a suitable organic solvent.
    Type: Grant
    Filed: February 18, 1982
    Date of Patent: December 13, 1983
    Assignee: FMC Corporation
    Inventors: Borivoj R. Franko-Filipasic, James Snyder
  • Patent number: 4390733
    Abstract: The mono-methallyl ether of pyrocatechin of formula (I): ##STR1## is prepared by reacting pyrocatechin of formula (II): ##STR2## with a methallyl halide of formula (III): ##STR3## in a homogeneous dissolving medium, e.g., alcohols, aliphatic polyalcohols and monoethers thereof, or water, in the presence of an organic or inorganic base.The mono-methallyl ether of pyrocatechin is used as an intermediate for organic syntheses and, in particular for synthesizing the product of formula (IV); ##STR4## which is marketed under the tradename "Carbofuran" and is a compound which is the active principle in soil insecticides of different overall compositions which are available on the market.
    Type: Grant
    Filed: May 14, 1981
    Date of Patent: June 28, 1983
    Assignee: Montedison S.p.A.
    Inventors: Stefano Campolmi, Vittorio Carletti, Marcello Marchi
  • Patent number: 4383126
    Abstract: A process for the preparation of a monoalkyl ether of a hydroxyphenol of the formula ##STR1## in which Z each independently is hydrogen or a substituent which is stable under the reaction conditions,R is lower alkyl, andn is 1, 2, 3 or 4,comprising reacting a hydroxyphenol of the formula ##STR2## with an alkyl halide, alkyl sulphonate or aryl sulphonate alkylating agent of the formulaR--Xin which X is a halogen atom, or an alkylsulphonyloxy or arylsulphonyloxy radical,at a temperature from about 130.degree. C. to 200.degree. C. and in the presence of an alkali metal base or alkaline earth metal base and of a diluent comprising a polyhydroxyalkyl ether having at least one OH group. Advantageously the base is sodium carbonate, sodium bicarbonate, potassium carbonate or potassium bicarbonate, the hydroxyphenol is pyrocatechol, the alkylating agent is isopropyl chloride, isopropyl C.sub.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: May 10, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Buttner, Artur Judat, Udo Allenbach, Manfred Lenthe
  • Patent number: 4360469
    Abstract: It has been found that unexpectedly high yields of a high purity product can be obtained when substituted p-quinones are prepared by oxidation, using a molecular oxygen-containing gas, of the corresponding phenols in an inert solvent having a dipole moment of at least 2.7 and in the presence of a salcomine catalyst.
    Type: Grant
    Filed: June 11, 1970
    Date of Patent: November 23, 1982
    Assignee: Eastman Kodak Company
    Inventors: Hans K. Dietl, Howard S. Young
  • Patent number: 4346040
    Abstract: The invention relates to a process for converting an aldehyde into a corresponding alkene and of the type wherein the aldehyde is placed in the presence of a phosphoric reagent and a base in solution in an organic aprotic solvent; the process comprising using a mineral base evincing in an aqueous medium a basic force less than or equal to that of the hydroxide ion or a strongly basic organic base of the nitrogen compounds family and adjusting the hydration rate of the reaction medium in such a manner that there are about 0.5 to 5 moles of water per mole of aldehyde.
    Type: Grant
    Filed: July 21, 1981
    Date of Patent: August 24, 1982
    Assignee: Agrifurane S.A.
    Inventors: Michel Delmas, Antoine Gaset, Yves Le Bigot
  • Patent number: 4335263
    Abstract: A process for preparing an aromatic aldehyde represented by the following general formula: ##STR1## wherein R.sub.1 and R.sub.2 each represents a hydrogen atom or a lower alkyl group or R.sub.1 and R.sub.2 may jointly form an alkylene group, provided that R.sub.1 and R.sub.2 do not represent a hydrogen atom at the same time.
    Type: Grant
    Filed: December 19, 1980
    Date of Patent: June 15, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Masayoshi Minai
  • Patent number: 4314086
    Abstract: Aliphatic/aromatic ethers are prepared by reacting an aliphatic halide with either an alkali or alkaline earth metal, or ammonium phenolate or naphtholate, in an inert organic solvent, and in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.
    Type: Grant
    Filed: June 20, 1980
    Date of Patent: February 2, 1982
    Assignee: Rhone-Poulenc Industries
    Inventors: Gerard Soula, Daniel Michelet
  • Patent number: 4307253
    Abstract: Procecss for the preparation of alkyl aryl ethers by reacting phenols with aliphatic ethers in the presence of strongly acid cation exchangers.
    Type: Grant
    Filed: January 7, 1980
    Date of Patent: December 22, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Neumann, Hans-Helmut Schwarz, Dieter Nachtsheim
  • Patent number: 4302615
    Abstract: A reductive hydrogenolysis of a 2-substituted 1,3-benzodioxole is carried out employing a hydride-donating reducing agent system to produce a 2-alkoxyphenol.
    Type: Grant
    Filed: August 5, 1980
    Date of Patent: November 24, 1981
    Assignee: S. C. Johnson & Son, Inc.
    Inventor: John D. Hagarty
  • Patent number: 4283565
    Abstract: There is described an essentially two step process for the preparation of benzylalcohols including those benzylalcohols having substituents on the benzyene ring by reaction of a substituted or unsubstituted benzyl halide with a formate typically an alkali or alkaline earth metal formate to form the corresponding substituted or unsubstituted benzyl formate. In the second step of the process the benzyl formate is contacted with an alcohol whereby the same is converted into the desired benzylalcohol. Both steps can be performed employing catalysts. Described in the specification is the realization of the desired product in exceptionally high yields in a short period of time whereby the process is characterized by high space-time yields.
    Type: Grant
    Filed: December 29, 1978
    Date of Patent: August 11, 1981
    Assignee: Dynamit Nobel AG
    Inventors: Gunther Bernhardt, Gerhard Daum
  • Patent number: 4271090
    Abstract: The novel bis (2-bromoethyl) tellurium dibromide and 2-bromoethyl tellurium tribromide are prepared by reacting ethylene with a source of tellurium tetrabromide in an inert, non-basic organic solvent under certain temperature conditions and in the substantial absence of molecular oxygen.
    Type: Grant
    Filed: October 29, 1979
    Date of Patent: June 2, 1981
    Assignee: Halcon Research and Development Corp.
    Inventors: Anthony N. Naglieri, Nabil Rizkalla
  • Patent number: 4263462
    Abstract: Unsaturated ethers of diphenols are prepared from alkenyl halides and diphenols as reagents and by carrying out the reaction in two zones at different temperatures.Intermediates for perfumes, aromas and insecticides are so prepared.
    Type: Grant
    Filed: November 7, 1979
    Date of Patent: April 21, 1981
    Assignee: Philagro
    Inventors: Daniel Michelet, Michel Rakoutz
  • Patent number: 4254288
    Abstract: A method of producing an aromatic compound comprises dehydrogenating a compound having a six-membered carbocyclic ring in the molecule, the ring having a degree of saturation greater than that of a benzene ring, the dehydrogenation being carried out in the presence of a catalyst system comprising elemental palladium together with sodium carbonate and sulphur. The compound to be dehydrogenated may be a substituted cyclohexane. When the substituted cyclohexane is an alkoxycyclohexanol, the aromatic compound produced is an alkoxy phenol. In particularly useful aspect of the invention the substituted cyclohexane is a 2-alkoxycyclohexanol, the aromatic compound produced being an ortho-alkoxy phenol.
    Type: Grant
    Filed: July 6, 1979
    Date of Patent: March 3, 1981
    Assignee: Coalite Group Limited
    Inventor: Keith Gladwin
  • 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: 4250333
    Abstract: Process for the selective monoetherification of pyrocatechol.The process relates to the selective monoetherification of pyrocatechol by means of methallyl chloride.It consists of carrying out the etherification in an aprotic solvent medium in the presence of an alkali metal carbonate or bicarbonate.The process can be used industrially for the preparation of o-methallyloxyhenol.
    Type: Grant
    Filed: October 12, 1978
    Date of Patent: February 10, 1981
    Assignee: Philagro
    Inventor: Michel Rakoutz
  • Patent number: 4241225
    Abstract: Alkanols, alkylamines or hydroxylamines are reacted with a cycloalkene oxide in the presence of Fuller's earth as a catalyst to prepare, respectively, 2-cycloalkanol ethers, 2-alkylamino-cycloalkanols, or 2-hydroxylamino-cycloalkanols.
    Type: Grant
    Filed: June 6, 1978
    Date of Patent: December 23, 1980
    Assignee: Coalite and Chemical Products Limited
    Inventor: Keith Gladwin
  • Patent number: 4220605
    Abstract: A process for the production of alcohols and/or aldehydes which comprises subjecting a toluene derivative having an ether linkage or linkages of the general formula: ##STR1## wherein RO is an ether grouping where R stands for a hydrocarbyl group with 1.about.20 carbon atoms which may carry an inert substituent or substituents and n stands for an integer of 1.about.2, to auto-oxidation with molecular oxygen in liquid phase to form the corresponding alcohol and/or aldehyde, characterized in that the reaction is carried out by using a lower saturated fatty acid and/or an anhydride thereof as solvent in the presence of a soluble cobalt salt and a bromine ion-supplying substance at a reaction temperature ranging from 30.degree. C. to 200.degree. C. in such manner that the conversion rate of the toluene derivative does not exceed 90%.
    Type: Grant
    Filed: December 23, 1977
    Date of Patent: September 2, 1980
    Assignees: Director General of Agency of Industrial Science and Technology, Sanko Chemical Co. Ltd., Nippon Soda Co. Ltd.
    Inventor: Juichi Imamura
  • Patent number: 4199531
    Abstract: A novel method for producing hydroquinone and quinone derivatives by a regio- and stereo-specific coupling reaction of hydroquinone derivative having a terminal activated (poly)prenyl side chain with a prenyl derivative. This method can provide in good yield various hydroquinone and quinone derivatives having any prenyl length of the side chain.
    Type: Grant
    Filed: October 11, 1977
    Date of Patent: April 22, 1980
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Kaneyoshi Kato
  • Patent number: 4192949
    Abstract: Phenol ethers are prepared by reacting phenols with dialkyl carbonates in the presence of tertiary amines and/or phosphines. The aralkyl aryl ethers and alkyl aryl ethers obtained are starting materials for the manufacture of dyes, crop protection agents and scents.
    Type: Grant
    Filed: June 15, 1978
    Date of Patent: March 11, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Friedrich Towae, Ludwig Schroff, deceased
  • Patent number: 4166914
    Abstract: O-alkoxyphenols are produced from cyclohexanone or cyclohexanol by chlorination of cyclohexanone or cyclohexanol to trichlorocyclohexanone and reaction of the trichlorocyclohexanone with an aliphatic, monohydric alcohol having one to four carbon atoms and a base to form an intermediate compound or compounds which are further reacted to convert the intermediate compound or compounds to an o-alkoxyphenol.
    Type: Grant
    Filed: May 31, 1977
    Date of Patent: September 4, 1979
    Assignee: Carl E. Van Winckel
    Inventors: Carl E. Van Winckel, David H. Dolphin, Elena Dumitrescu, Kent F. Van Winckel
  • Patent number: 4162326
    Abstract: Compounds having the formula ##STR1## in which one of R.sub.1 and R.sub.2 is C.sub.3 -C.sub.4 alkynoxy or C.sub.3 alkenoxy and the other is hydrogen or methoxy. The compounds have utility as insect control agents, either as insecticides or anti-juvenile hormones.
    Type: Grant
    Filed: September 27, 1978
    Date of Patent: July 24, 1979
    Assignee: Stauffer Chemical Company
    Inventor: Alexander Mihailovski
  • Patent number: 4154769
    Abstract: The invention concerns a new process for the production of 2-alkoxy-4-propen-1-yl phenols of the formula ##STR1## in which R represents the methyl or ethyl radical wherein 2-alkoxy phenols of the formula ##STR2## in which R is as defined above, are initially condensed with propionaldehyde in the presence of acid catalysts, and the resulting condensation product is subsequently split by heating in the presence of a basic catalyst to form the phenols of formula I.
    Type: Grant
    Filed: March 21, 1977
    Date of Patent: May 15, 1979
    Assignee: Haarmann & Reimer GmbH
    Inventors: Kurt Bauer, Reiner Molleken, Rudolf Hopp
  • 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: 4129601
    Abstract: New and valuable pyrocatechol derivatives and a process for their preparation. The pyrocatechol derivatives have the formula ##STR1## wherein: R denotes alkyl of from 1 to 4 carbon atoms which may be substituted with halogen; alkenyl having up to 4 carbon atoms which may be substituted with halogen; alkynyl having up to 5 carbon atoms which may be substituted with halogen; or benzyl;R.sup.1 denotes hydrogen or alkyl of from 1 to 4 carbon atoms;R.sup.2 denotes benzyl or alkyl of from 1 to 3 carbon atoms which may be substituted with halogen, methoxy or ethoxy;R.sup.3 denotes alkyl of from 1 to 4 carbon atoms; cycloalkyl of from 3 to 7 carbon atoms; .beta.-chlorethyl; methoxyethyl; ethoxyethyl; alkenyl of from 2 to 4 carbon atoms; alkynyl of from 2 to 4 carbon atoms; acetyl; propionyl;R.sup.1 and R.sup.2 when taken together with the carbon atom to which they are attached form a cyclopentyl or cyclohexyl ring; andR.sup.1 and R.sup.
    Type: Grant
    Filed: August 2, 1976
    Date of Patent: December 12, 1978
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl Kiehs, Rolf Huber