Ether Oxygen Is Ortho To The Hydroxy Patents (Class 568/652)
-
Patent number: 5015769Abstract: 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: GrantFiled: June 19, 1990Date of Patent: May 14, 1991Assignee: L'OrealInventors: Alex Junino, Gerard Lang, Alain Genet
-
Patent number: 4982012Abstract: 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: GrantFiled: December 18, 1987Date of Patent: January 1, 1991Assignee: FMC CorporationInventor: John W. Ager, Jr.
-
Patent number: 4959391Abstract: 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: GrantFiled: July 14, 1988Date of Patent: September 25, 1990Assignee: Gruenenthal GmbHInventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin O. Kiesewetter, Ulrich G. P. Seippl
-
Patent number: 4946865Abstract: 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: GrantFiled: December 24, 1986Date of Patent: August 7, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Junya Takahashi, Shigeko Nakamura
-
Patent number: 4851587Abstract: 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: GrantFiled: May 31, 1988Date of Patent: July 25, 1989Assignee: FMC CorporationInventors: Borivoj Franko-Filipasic, James Snyder
-
Patent number: 4820879Abstract: 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: GrantFiled: June 5, 1987Date of Patent: April 11, 1989Assignee: Lithium Corporation of AmericaInventor: Vijay C. Mehta
-
Patent number: 4760087Abstract: 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: GrantFiled: May 13, 1986Date of Patent: July 26, 1988Assignee: Gruenenthal GmbHInventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin Kiesewetter, Ulrich G. P. Seipp
-
Patent number: 4657700Abstract: 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: GrantFiled: September 21, 1984Date of Patent: April 14, 1987Assignee: Givaudan CorporationInventor: Paul A. Ochsner
-
Patent number: 4644085Abstract: 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: GrantFiled: June 4, 1985Date of Patent: February 17, 1987Assignee: Rooperol (NA) NVInventors: Siegfried Drewes, Roelof W. Liebenberg
-
Patent number: 4639536Abstract: 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: GrantFiled: August 30, 1984Date of Patent: January 27, 1987Assignee: Union Carbide CorporationInventors: Constance A. Fellows, Wallace Y. Fu
-
Patent number: 4618627Abstract: 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: GrantFiled: May 11, 1984Date of Patent: October 21, 1986Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Kiyoshi Murase, Toshiyasu Mase, Hideki Arima, Kenichi Tomioka
-
Patent number: 4618728Abstract: 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: GrantFiled: February 22, 1985Date of Patent: October 21, 1986Assignee: FMC CorporationInventors: Philip B. Hobson, Robert E. Keay
-
Patent number: 4599461Abstract: 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: GrantFiled: January 10, 1985Date of Patent: July 8, 1986Assignee: Brichima SpaInventors: Paolo Maggioni, Francesco Minisci, Mariano Correale
-
Patent number: 4588835Abstract: 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: GrantFiled: October 19, 1984Date of Patent: May 13, 1986Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Mitsuo Akada
-
Patent number: 4542229Abstract: 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: GrantFiled: April 11, 1983Date of Patent: September 17, 1985Assignee: Brichima S.p.A.Inventors: Paolo Maggioni, Francesco Minisci, Mariano Correale
-
Patent number: 4513109Abstract: 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: GrantFiled: January 27, 1984Date of Patent: April 23, 1985Assignee: Ciba-Geigy CorporationInventor: Siegfried Rosenberger
-
Patent number: 4501910Abstract: 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: GrantFiled: October 12, 1982Date of Patent: February 26, 1985Assignee: Agrifurane, S.A.Inventors: Michel Delmas, Antoine Gaset, Yves le Bigot
-
Patent number: 4487975Abstract: 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: GrantFiled: August 11, 1982Date of Patent: December 11, 1984Assignee: Rhone-Poulenc IndustriesInventor: Serge Ratton
-
Patent number: 4465867Abstract: 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: GrantFiled: June 11, 1982Date of Patent: August 14, 1984Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventors: Tsukasa Maekawa, Takeshi Gondo, Shigeo Takahashi, Hidetoshi Kume
-
Patent number: 4465868Abstract: 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: GrantFiled: June 11, 1982Date of Patent: August 14, 1984Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventors: Tsukasa Maekawa, Takeshi Gondo, Syozo Hayase
-
Patent number: 4420642Abstract: 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: GrantFiled: February 18, 1982Date of Patent: December 13, 1983Assignee: FMC CorporationInventors: Borivoj R. Franko-Filipasic, James Snyder
-
Patent number: 4390733Abstract: 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: GrantFiled: May 14, 1981Date of Patent: June 28, 1983Assignee: Montedison S.p.A.Inventors: Stefano Campolmi, Vittorio Carletti, Marcello Marchi
-
Patent number: 4383126Abstract: 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: GrantFiled: October 26, 1981Date of Patent: May 10, 1983Assignee: Bayer AktiengesellschaftInventors: Gerhard Buttner, Artur Judat, Udo Allenbach, Manfred Lenthe
-
Patent number: 4360469Abstract: 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: GrantFiled: June 11, 1970Date of Patent: November 23, 1982Assignee: Eastman Kodak CompanyInventors: Hans K. Dietl, Howard S. Young
-
Patent number: 4346040Abstract: 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: GrantFiled: July 21, 1981Date of Patent: August 24, 1982Assignee: Agrifurane S.A.Inventors: Michel Delmas, Antoine Gaset, Yves Le Bigot
-
Patent number: 4335263Abstract: 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: GrantFiled: December 19, 1980Date of Patent: June 15, 1982Assignee: Sumitomo Chemical Company, LimitedInventor: Masayoshi Minai
-
Patent number: 4314086Abstract: 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: GrantFiled: June 20, 1980Date of Patent: February 2, 1982Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Daniel Michelet
-
Patent number: 4307253Abstract: Procecss for the preparation of alkyl aryl ethers by reacting phenols with aliphatic ethers in the presence of strongly acid cation exchangers.Type: GrantFiled: January 7, 1980Date of Patent: December 22, 1981Assignee: Bayer AktiengesellschaftInventors: Rainer Neumann, Hans-Helmut Schwarz, Dieter Nachtsheim
-
Patent number: 4302615Abstract: 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: GrantFiled: August 5, 1980Date of Patent: November 24, 1981Assignee: S. C. Johnson & Son, Inc.Inventor: John D. Hagarty
-
Patent number: 4283565Abstract: 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: GrantFiled: December 29, 1978Date of Patent: August 11, 1981Assignee: Dynamit Nobel AGInventors: Gunther Bernhardt, Gerhard Daum
-
Patent number: 4271090Abstract: 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: GrantFiled: October 29, 1979Date of Patent: June 2, 1981Assignee: Halcon Research and Development Corp.Inventors: Anthony N. Naglieri, Nabil Rizkalla
-
Patent number: 4263462Abstract: 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: GrantFiled: November 7, 1979Date of Patent: April 21, 1981Assignee: PhilagroInventors: Daniel Michelet, Michel Rakoutz
-
Patent number: 4254288Abstract: 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: GrantFiled: July 6, 1979Date of Patent: March 3, 1981Assignee: Coalite Group LimitedInventor: Keith Gladwin
-
Patent number: 4252985Abstract: 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: GrantFiled: June 18, 1979Date of Patent: February 24, 1981Assignee: PhilagroInventor: Michel Rakoutz
-
Patent number: 4250333Abstract: 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: GrantFiled: October 12, 1978Date of Patent: February 10, 1981Assignee: PhilagroInventor: Michel Rakoutz
-
Patent number: 4241225Abstract: 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: GrantFiled: June 6, 1978Date of Patent: December 23, 1980Assignee: Coalite and Chemical Products LimitedInventor: Keith Gladwin
-
Patent number: 4220605Abstract: 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: GrantFiled: December 23, 1977Date of Patent: September 2, 1980Assignees: Director General of Agency of Industrial Science and Technology, Sanko Chemical Co. Ltd., Nippon Soda Co. Ltd.Inventor: Juichi Imamura
-
Patent number: 4199531Abstract: 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: GrantFiled: October 11, 1977Date of Patent: April 22, 1980Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Kaneyoshi Kato
-
Patent number: 4192949Abstract: 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: GrantFiled: June 15, 1978Date of Patent: March 11, 1980Assignee: BASF AktiengesellschaftInventors: Franz Merger, Friedrich Towae, Ludwig Schroff, deceased
-
Patent number: 4166914Abstract: 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: GrantFiled: May 31, 1977Date of Patent: September 4, 1979Assignee: Carl E. Van WinckelInventors: Carl E. Van Winckel, David H. Dolphin, Elena Dumitrescu, Kent F. Van Winckel
-
Patent number: 4162326Abstract: 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: GrantFiled: September 27, 1978Date of Patent: July 24, 1979Assignee: Stauffer Chemical CompanyInventor: Alexander Mihailovski
-
Patent number: 4154769Abstract: 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: GrantFiled: March 21, 1977Date of Patent: May 15, 1979Assignee: Haarmann & Reimer GmbHInventors: Kurt Bauer, Reiner Molleken, Rudolf Hopp
-
Patent number: 4139545Abstract: 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: GrantFiled: April 30, 1975Date of Patent: February 13, 1979Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroshi Morimoto, Isuke Imada, Masazumi Watanabe, Mitsuru Kawada
-
Patent number: 4138411Abstract: 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: GrantFiled: April 14, 1976Date of Patent: February 6, 1979Assignee: Rhone-Poulenc S. A.Inventor: Pierre Gandilhon
-
Patent number: 4129601Abstract: 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: GrantFiled: August 2, 1976Date of Patent: December 12, 1978Assignee: BASF AktiengesellschaftInventors: Karl Kiehs, Rolf Huber