Hydroxy Bonded Directly To The Benzene Ring (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/650)
  • Patent number: 5434314
    Abstract: Disclosed are novel polyether compounds obtained by the reaction or polymerization of 3,4-epoxy-1-butene in the presence of an acidic catalyst and a nucleophilic initiator compound. The polyether compounds comprise n units of residue (1) and m units of residue (2), wherein the total value of n+m is 2 to 70, n/(n+m) is a value in the range of 0.70 to 0.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: July 18, 1995
    Assignee: Eastman Chemical Company
    Inventors: James C. Matayabas, Jr., Stephen N. Falling
  • Patent number: 5416242
    Abstract: Novel hydroquinone derivatives of the formulae (I) and (II), ##STR1## wherein R.sup.1 is an alkyl group having 7 to 11 carbon atoms, ##STR2## wherein each of R.sup.2 to R.sup.5 is independently a hydrogen atom, a lower alkyl group or a lower alkoxy group provided that at least one of R.sup.2 to R.sup.5 is a lower alkyl group or a lower alkoxy group, and R.sup.6 is an alkyl group having a carbon chain of at least 2 carbon atoms. as compounds having antioxidant activity and tumor incidence inhibiting activity, and an antioxidant and a tumor incidence inhibitor containing, as an active ingredient, a hydroquinone derivative of the formula (III), ##STR3## wherein each of R.sup.7 to R.sup.10 is independently a hydrogen atom, a lower alkyl group or a lower alkoxy group, and R.sup.11 is an alkyl group having a carbon chain of at least 2 carbon atoms, and/or a salt thereof.
    Type: Grant
    Filed: August 1, 1994
    Date of Patent: May 16, 1995
    Assignee: Nippon Hypox Laboratories Incorporated
    Inventors: Toshio Satoh, Hitoshi Matsumoto, Yasunori Niiro
  • Patent number: 5414148
    Abstract: p-Nitrophenolic compounds, e.g., p-nitrophenol itself, are selectively prepared by (a) reacting a phenolic compound with a nitrosating agent in the presence of sulfuric acid, the concentration of which H.sub.2 SO.sub.4 being at least 60%, (b) oxidizing the p-nitrosophenolic compound thus formed with nitric acid, the concentration of sulfuric acid in the medium of reaction, upon completion of oxidation, being no greater than 80%, and (c) separating the p-nitrophenolic compound which thus precipitates.
    Type: Grant
    Filed: May 26, 1994
    Date of Patent: May 9, 1995
    Assignee: Rhone-Poulenc Chimie
    Inventors: Pascal Metivier, Laurent Bernard
  • Patent number: 5414153
    Abstract: Phenolic compounds, e.g., the phenols and phenol ethers, are selectively hydroxylated whereby the amounts of the final product para isomer are enhanced, for example in favor of hydroquinone versus pyrocatechol in the event of the hydroxylation of phenol, by reacting such phenolic compounds with hydrogen peroxide, advantageously in a polar, aprotic, organic solvent reaction medium, in the presence of a catalytically effective amount of a sulfonated polymer and a cocatalytically effective amount of an aromatic ketone compound.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: May 9, 1995
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Dominique Laucher
  • Patent number: 5393776
    Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: February 28, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventor: Bradley C. Pearce
  • Patent number: 5387718
    Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: February 7, 1995
    Assignee: Huels Aktiengesellschaft
    Inventors: Gunther Kohler, Peter Bickert
  • Patent number: 5319148
    Abstract: The preparation of pyrocatechol monoethers or pyrocatechols of the formula Ia or Ib respectively ##STR1## ( R.sup.1 and R.sup.2 =H or C.sub.1 --C.sub.8 -hydrocarbon radicals; R.sup.3 =C.sub.1 --C.sub.8 -hydrocarbon radical ) by rearranging a 2-hydroxycyclohexanone dialkyl ketal II ##STR2## a) in the gas phase in the presence of a platinmetal or in the presence of a compound of one of these metals as catalyst in order to obtain a compound Ia, orb) carrying out step a) in the presence of water in order to obtain a compound Ib. The products are used as intermediates in the synthesis of pharmaceuticals, fragrances and flavors.
    Type: Grant
    Filed: March 2, 1993
    Date of Patent: June 7, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Karcher, Horst Zimmermann, Jochem Henkelmann
  • Patent number: 5254747
    Abstract: Compounds are provided which comprise a fluorocarbon terminal portion and a chiral hydrocarbon terminal portion, said terminal portions being connected by a central core, said compounds having tilted smectic mesophases or having latent tilted smectic mesophases which develop when said compounds having said latent mesophases are in admixture with said compounds having tilted smectic mesophases or said compounds having latent tilted smectic mesophases.
    Type: Grant
    Filed: May 21, 1991
    Date of Patent: October 19, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Eugene P. Janulis
  • Patent number: 5248835
    Abstract: A monoalkylether of a dihydric phenol compound is produced at a high conversion and selectivity by catalytically dehydration reacting a dihydric phenol compound with a lower monohydric alcohol in the presence of a catalyst comprising at least one inorganic substance of the empirical formula (I):Al.sub.a P.sub.b Ti.sub.c Si.sub.d X.sub.e O.sub.f (I):wherein X is an alkali metal (Group Ia) atom, alkaline earth metal (Group IIa) atom or a metal atom of Group VIII of the Periodic Table, a, b, c, d, e and f are the numbers of Al, P, Ti, Si, X and O atoms respectively, and provided that a =1, b =1.0 to 1.9, c =0 05 to 0.5, d=0.05 to 0.2, e=0 to 0.9 and f=4.2 to 8.1, and collecting the resultant reaction product from the reaction system.
    Type: Grant
    Filed: April 16, 1992
    Date of Patent: September 28, 1993
    Assignee: Ube Industries, Ltd.
    Inventors: Yasushi Shiomi, Yasuo Nakamura, Takumi Manabe, Shinichi Furusaki, Masaoki Matsuda, Muneki Saito
  • Patent number: 5245089
    Abstract: Provided is a process for alkylating aromatic compounds in the presence of mixed oxides of titanium and gallium which have been found to be highly active catalysts for the alkylation of aromatics with alkyl esters, alcohols, olefins and ethers. When the alkyl acceptor is a phenol, the catalysts provide high reaction rates and high selectivity for ortho alkylated products.
    Type: Grant
    Filed: October 23, 1992
    Date of Patent: September 14, 1993
    Assignee: Eastman Kodak Company
    Inventors: Gether Irick, Jr., Leslie S. LaForce
  • Patent number: 5233097
    Abstract: Certain crystalline titanoaluminosilicate molecular sieve compositions having titanium, aluminum, and silicon present as framework tetrahedral oxide units are particularly effective in hydroxylating the aromatic nucleus of aromatic compounds using hydrogen peroxide, even where the hydrogen peroxide is used at concentrations of 10 weight percent or less. The variant where the exchangeable hydrogens of the titanoaluminosilicate are replaced by an alkali or alkaline earth metal cation is particularly favored because of the concomitant increase in selectivity. Excellent utilization of hydrogen peroxide often is observed, even when the hydroxylation is effected at temperatures under about 60.degree. C.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: August 3, 1993
    Assignee: UOP
    Inventors: Laszlo T. Nemeth, Eric M. Hyatt, Thomas P. Malloy
  • Patent number: 5189225
    Abstract: A monoalkylether of dihydric phenol compound is produced by bringing a feed gas comprising a mixture gas of a dihydric phenol compound with a monohydric alcohol compound into contact with an active catalyst component comprising at least one member selected from phosphorus compounds, and mixtures and reaction products of phosphorus compounds with boron compounds and carried on an inert solid carrier consisting of, for example, .alpha.-alumina, .gamma.-alumina, activated carbon or titania grains, and preferably having a pore volume of 0.1 ml/g or more and a specific surface area of 1 m.sup.2 /g or more, at a temperature of 200.degree. C. to 400.degree. C., and collecting the resultant reaction product from the reaction mixture.
    Type: Grant
    Filed: September 28, 1990
    Date of Patent: February 23, 1993
    Assignee: Ube Industries, Ltd.
    Inventors: Shinichi Furusaki, Masaoki Matsuda, Muneki Saito, Yasushi Shiomi, Yasuo Nakamura, Michio Tobita
  • Patent number: 5149888
    Abstract: The phenols and phenol ethers, e.g., phenol itself, are effectively hydroxylated by reacting hydrogen peroxide therewith, in the presence of a catalytically effective amount of titanium dioxide.
    Type: Grant
    Filed: February 28, 1990
    Date of Patent: September 22, 1992
    Assignee: Rone-Poulenc Chimie
    Inventors: Michel Costantini, Eric Garcin, Michel Gubelmann, Jean-Michel Popa
  • Patent number: 5146010
    Abstract: A process for removing guaiacols from naturally-occurring cresylic acid mixtures by pyrolysis is described.
    Type: Grant
    Filed: August 9, 1991
    Date of Patent: September 8, 1992
    Assignee: Merichem Company
    Inventors: James A. Brient, Marvin H. Strunk, Jr.
  • Patent number: 5082978
    Abstract: Mono-, di- and triphenols are selectively monomethylated by reaction with para-dimethoxybenzene in the presence of a catalytically effective amount of an acid catalyst.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: January 21, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Gubelmann, Christian Allandrieu
  • Patent number: 5025095
    Abstract: Substituted diallylphenol derivatives are useful as reactive diluents for bismaleimides. Formulations comprising bismaleimides and substituted diallylphenol derivatives are particularly useful in resin transfer molding and filament winding techniques.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: June 18, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Yefim Blyakhman, Byung H. Lee
  • Patent number: 4973764
    Abstract: There are disclosed novel compositions of matter comprising monoalkylphenols prepared by selectively alkylating the olefin component of a thermally cracked sulfur-containing petroleum distillate derived from residua. The monoalkylphenols have certain ortho to para ratios and may be used to prepare a number of useful derivatives such as ethoxylated and propoxylated surfactants, sulfoalkylated products, sulfurized antioxidants, overbased phenates, dithiophosphate derivatives, formaldehyde reaction products and similar methylene bridged products which are useful demulsifiers.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: November 27, 1990
    Assignee: Exxon Research and Engineering Company
    Inventors: Alexis A. Oswald, Ram N. Bhatia, Edmund J. Mozeleski, Darrell W. Brownawell, Thomas L. Ashcraft
  • Patent number: 4971995
    Abstract: Pharmaceutical or veterinary preparations containing (a) at least one compound with the formula: ##STR1## where:R.sub.o represents a C.sub.3 -C.sub.6 alkyl group or a benzyl group with the formula: ##STR2##in which R.sub.3 =H, a halogen, a C.sub.1 -C.sub.4 alkyl, a C.sub.1 -C.sub.4 alkoxy, CF.sub.3, NO.sub.2 or a CN group; andR.sub.2 represents:a C.sub.1 -C.sub.4 alkoxy group, in which case the pair (X, R.sub.1)=(O, OH), (O, C.sub.1 -C.sub.4 alkoxy), (CHOH, H), (O, H), (CH.sub.2, H) or (CO, H);and OH group, in which case the pair (X, R.sub.1)=(O, OH), (O, C.sub.1 -C.sub.4 alkoxy), (O, H) or (CH.sub.2, H), with the reservation that when (X, R.sub.1)=(O, OH), R.sub.o is different from a C.sub.3 -C.sub.6 alkyl or a benzyl group; ora CN or C.sub.1 -C.sub.4 alkyl-NH group, in which case the pair (X, R.sub.1)=(O, H) or (CH.sub.2, H), together with (b) a carrier or vehicle which is physiologically acceptable and appropriate for the compound used.
    Type: Grant
    Filed: January 26, 1989
    Date of Patent: November 20, 1990
    Assignee: Delande S.A.
    Inventors: Alain R. Schoofs, Michel Langlois, Christian R. Jeanpetit, Maryse F. Masson
  • Patent number: 4960946
    Abstract: The present invention relates to novel substituted cyclohexanol compounds possessing a sandalwood aroma which are useful as fragrance materials. The invention also provides methods for synthesis thereof through a novel aldehyde intermediate. The compounds of the invention have the formula: ##STR1## wherein A is ##STR2## and wherein R.sub.1 is methyl or ethyl, R.sub.2 -R.sub.7 are independently hydrogen or methyl with the proviso that a maximum of two of the substituents R.sub.2 -R.sub.7 are methyl, and R.sub.8 is hydrogen, lower alkyl (C.sub.1 to C.sub.5) or acyl. The invention also provides fragrance compositions which utilize the compounds of the invention to impart a sandalwood aroma to perfume compositions, colognes and perfumed articles.
    Type: Grant
    Filed: October 13, 1989
    Date of Patent: October 2, 1990
    Assignee: BASF K&F
    Inventors: Robert Eilerman, Philip Christenson, John Yurecko, Jr., Thomas Zebovitz
  • 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: 4954659
    Abstract: A grignard synthesis of pharmacologically active 1,4-bis(dihydroxyphenyl)butane and analogs, as well as novel intermediates, is provided, comprising preparing a grignard reagent preferably, a 3,4-dialkoxyphenyl propyl magnesium bromide, which may be reacted with carbonyl compounds to form intermediates of desired end products, said carbonyl compounds preferably being 3,4-dialkoxybenzaldehydes. The resulting alcohol is converted to a corresponding ether or siloxy compound, at the carbonyl site. The oxy-substituent is cleaved off; and the benzene ring or rings dealkylated to leave hydroxy substituents on the rings.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: September 4, 1990
    Assignee: Chemex Pharmaceuticals, Inc.
    Inventors: Robert M. Parkhurst, Ronald S. Pardini
  • Patent number: 4954662
    Abstract: Ortho-substituted phenolic compounds, e.g., 2,6-dichlorophenol, are selectively chlorinated, e.g., into 2,4,6-trichlorophenol, with gaseous chlorine in either the molten state or in a solvent medium, in the presence of a selectivity-enhancing effective amount of an organic cation.
    Type: Grant
    Filed: July 18, 1988
    Date of Patent: September 4, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Roger Desmurs, Bernard Besson, Isabelle Jouve
  • Patent number: 4933504
    Abstract: Mono-ethers of hydroquinones of formula (I) ##STR1## wherein R represents alkyl, alkoxy-alkyl, cycloalkyl, aryl-alkyl, or cycloalkyl-alkyl, andR.sup.1 is hydrogen or alkyl, cycloalkyl, aryl-alkyl, or cycloalkyl-alkyl, are prepared by contacting the corresponding hydroquinones with the corresponding alcohols ROH, in the presence of a catalytic mixture consisting of(a) a strong acid(b) a halogen or a hydrohalic acid selected from HBr, HI, I.sub.2, and Br.sub.2, and(c) H.sub.2 O.sub.2 in a molar amount lower than that of the starting hydroquinone.
    Type: Grant
    Filed: November 25, 1988
    Date of Patent: June 12, 1990
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Mariano Correale, Pietro Panseri, Ugo Romano, Francesco Minisci
  • Patent number: 4825011
    Abstract: The nuclear hydroxylation of substituted phenols is performed by using aqueous hydrogen peroxide in the presence of sulfur dioxide or selenium dioxide as catalyst in a simple manner with very good space-time yields and good product yields.
    Type: Grant
    Filed: December 4, 1987
    Date of Patent: April 25, 1989
    Assignee: Degussa AG
    Inventors: Karl-Heinz Drauz, Axel Kleeman, Gunter Prescher, Gebhard Ritter
  • 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: 4751332
    Abstract: Resorcinol and substituted resorcinols are converted in one single step reaction into 1,2,3- and 1,2,4-trihydroxybenzenes and substituted hydroxy resorcinol compounds with a benzene solution of peroxypropionic acid.
    Type: Grant
    Filed: September 14, 1987
    Date of Patent: June 14, 1988
    Assignee: Degussa Aktiengesellschaft
    Inventors: Guenter Prescher, Gebhard Ritter, Holger Sauerstein
  • Patent number: 4668829
    Abstract: Ferroelectric (chiral) smectic liquid crystal compounds having an achiral core and chiral tail units derived from lactic acid possess the desired combination of properties temperature range, ferroelectric polarization, and low orientational viscosity. These newly made compounds exhibit high speed, multistate electro-optic switching properties which make them ideally suited to certain electro-optic and display device applications.
    Type: Grant
    Filed: September 17, 1985
    Date of Patent: May 26, 1987
    Assignee: University Patents, Inc.
    Inventor: David M. Walba
  • Patent number: 4663489
    Abstract: The cobalt carbonyl catalyst R.sup.5 CCo.sub.3 (CO).sub.9, desirably with Ru.sub.3 (CO).sub.12, wherein R.sup.5 is hydrogen; alkyl, preferably C.sub.1-5 lower alkyl; cycloalkyl or substituted cycloalkyl; cycloalkenyl, such as cyclohexenyl or cyclooctenyl; C.sub.1-12 alkoxy, such as methoxy or propoxy; aryl or alkyl-, cycloalkyl-, alkoxy-, halo-, or cyano-substituted aryl; cyano; or a silyl carbyne moiety of the formula R.sub.3.sup.6 Si, wherein R.sup.6 is alkyl or aryl, effectively catalyzes the dealkoxyhydroxymethylation of aldehyde acetals to form glycol monoethers. Methylal, for example, may be reacted with syngas; i.e., CO and H.sub.2, in the presence of this catalyst system to form the corresponding ethylene glycol monomethyl ether.The novel catalyst combination of R.sup.5 CCo.sub.3 (CO).sub.9 and Ru.sub.3 (CO).sub.12 is likewise claimed herein.
    Type: Grant
    Filed: May 5, 1986
    Date of Patent: May 5, 1987
    Assignee: Sun Refining and Marketing Company
    Inventors: D. Michael Duggan, Harry K. Myers, Jr., James E. Lyons
  • Patent number: 4652563
    Abstract: This invention relates to dihydropyridazinone compounds having a cyclopropylmethoxyethyl group in the 6-substituent. These compounds are vasodilators and .beta.-adrenoceptor antagonists. A particular compound of the invention is 6-[4-[3-[2-hydroxy-3-[4-(2-(cyclopropylmethoxy) ethyl)phenoxy]propylamino]propionamido]phenyl]-5-methyl-4,5-dihydro-3 (2H)-pyridazinone.
    Type: Grant
    Filed: May 16, 1985
    Date of Patent: March 24, 1987
    Assignee: Smith Kline & French Laboratories Ltd.
    Inventor: Robert A. Slater
  • Patent number: 4650604
    Abstract: Perfume compositions and perfumed products characterized by a content of one or more fragrances which have the characteristic odor of vanilla and correspond to the formula ##STR1## wherein R.sub.1 or R.sub.2 represents a hydrogen atom and the other symbol an ethyl or propyl group and R.sub.3 represents a methyl or ethyl group.
    Type: Grant
    Filed: October 16, 1985
    Date of Patent: March 17, 1987
    Assignee: Naarden International N. V.
    Inventors: Nicolaas L. J. M. Broekhof, Antonius J. A. van der Weerdt
  • 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: 4616082
    Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and Q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification,The new compounds are useful e.g. as stabilizers in photographic material.
    Type: Grant
    Filed: June 7, 1985
    Date of Patent: October 7, 1986
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4610996
    Abstract: Phenoxytriazolyl ketones and carbinols of the formula ##STR1## in which A represents the keto group or the CH(OH) grouping andR represents hydrogen, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, alkylcarbonyl, optionally substituted benzyl or optionally substituted phenoxymethyl,or addition products thereof with acids or metal salts, which possess fungicidal activity.
    Type: Grant
    Filed: April 11, 1984
    Date of Patent: September 9, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Kraatz, Karl H. Buchel, Paul Reinecke, Wilhelm Brandes, Gerd Hanssler
  • Patent number: 4598160
    Abstract: A catalytic synthesis of chromans in racemic or optically active forms, including intermediates thereto; the synthesis employs an asymmetric palladium (II) catalyzed oxidative cyclization of a 2-homoallylphenol and provides intermediates useful in making chromans, especially vitamin E in racemic or optically active forms.
    Type: Grant
    Filed: March 11, 1985
    Date of Patent: July 1, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Larry K. Truesdale
  • Patent number: 4594460
    Abstract: Substituted phenols of formula ##STR1## in which R.sub.1 is in an ortho or para position relative to the phenol function and denotes ##STR2## R.sub.2 denotes an acyclic radical optionally substituted by alkyl, hydroxy, alkoxycarbonyl, cyano or formyl, or a phenyl or naphthyl radical, and R denotes hydrogen or 1 to 4 substituents chosen from halogen, OH optionally in the form of ether or ester, alkyl, NO.sub.2, CHO optionally in the form of acetal, CH.sub.3 CO--, C.sub.6 H.sub.5 CO--, NH.sub.2, alkylamino, dialkylamino or alkoxycarbonyl, it being understood that 2 symbols R may form with the phenyl nucleus a condensed aromatic ring, which comprises reacting a butadiene of formula ##STR3## with a phenol for formula ##STR4## in water in the presence of a rhodium-based catalyst, a water-soluble phosphine and optionally an inorganic or organic base. The products of formula (I) are intermediates for the synthesis of vitamin E, antioxidants, perfumes or insecticides.
    Type: Grant
    Filed: March 19, 1985
    Date of Patent: June 10, 1986
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • 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: 4568497
    Abstract: Preparation of monoethers of dihydroxybenzenes from an alkenylphenol and an alkylating agent and thereafter oxidizing in the presence of an acid catalyst.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: February 4, 1986
    Assignee: The Dow Chemical Company
    Inventors: Abel Mendoza, Eric W. Otterbacher
  • Patent number: 4558129
    Abstract: Novel compounds of the general formula: ##STR1## and the pharmaceutically acceptable esters and acid addition salts thereof, wherein:R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are each independently hydrogen, lower alkyl, lower alkoxy, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl, lower alkyl sulfonyl; orR.sup.2 and R.sup.3 together form --OCH.sub.2 O--; andR.sup.10 and R.sup.11 are each independently hydrogen or lower alkyl.These compounds combine .beta.-blockade and calcium entry blockade properties in the same compound and therefore are useful in therapy in the treatment of cardiovascular diseases, including hypertension, arrhythmias and variant and exercise induced angina.
    Type: Grant
    Filed: May 18, 1983
    Date of Patent: December 10, 1985
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Arthur F. Kluge, Robin D. Clark, Arthur M. Strosberg
  • Patent number: 4538002
    Abstract: There is disclosed a process for the production of alkylated hydroxyanisoles which consists of dehydrogenating para-isopropylphenol to para-isopropenylphenol which is then reacted with a methylating agent to yield para-isopropenylanisole which is then treated with acidic hydrogen peroxide to yield para-hydroxyanisole which is then treated with an alkylating agent to yield the alkylated hydroxyanisole. The process of this invention is especially useful for the synthesis of the food preservative butylated hydroxyanisole (BHA).
    Type: Grant
    Filed: September 10, 1984
    Date of Patent: August 27, 1985
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Howard A. Colvin, Joel Muse, Jr., William S. Hollingshead
  • Patent number: 4528394
    Abstract: Prepare hydroxyaromatic ethers by contacting an oxidizing agent with an acylaromatic ether in the presence of an acid catalyst.
    Type: Grant
    Filed: August 3, 1983
    Date of Patent: July 9, 1985
    Assignee: The Dow Chemical Company
    Inventor: Eric W. Otterbacher
  • 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: 4511731
    Abstract: Preparation of monoethers of dihydroxybenzenes from an isopropenylphenol and an alkylating agent and thereafter oxidizing in the presence of an acid catalyst.
    Type: Grant
    Filed: June 24, 1983
    Date of Patent: April 16, 1985
    Assignee: The Dow Chemical Company
    Inventors: Abel Mendoza, Eric W. Otterbacher
  • Patent number: 4504685
    Abstract: Hydroxyl compounds are oxyalkylated by contacting them with an alkylene oxide, such as ethylene oxide or propylene oxide, in the presence of a perfluorocarbon polymer containing pendant sulfonic acid groups.
    Type: Grant
    Filed: August 19, 1980
    Date of Patent: March 12, 1985
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4495353
    Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula -O-R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: January 22, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Robert J. Bryant
  • 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: 4486611
    Abstract: A process for the isolation of a dihydroxybenzene-monoether from a reaction mixture containing solvent, ether and unreacted dihydroxybenzene, comprising contacting the reaction mixture with at least one hydrocarbon which is not miscible or only partially miscible with the reaction mixture, the ether selectively entering the hydrocarbon. Advantageously the reaction for the preparation of the monoether is carried out in an alcohol, a ketone, a dipolar aprotic solvent or a polyhydroxyalkyl ether, or a mixture thereof with water, the hydrocarbon used as extracting agent has a boiling point between about 80.degree. and 300.degree. C., and the extraction is carried out in the presence of water whereby there is an increase in the selectivity of the extraction.
    Type: Grant
    Filed: August 30, 1982
    Date of Patent: December 4, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Lenthe, Udo Allenbach, Gerhard Buttner, Karl-Friedrich Christmann
  • Patent number: 4473713
    Abstract: At least one of the other functions comprising an aryl-aliphatic ether, e.g., veratrol, is catalytically hydrolyzed with water, e.g., to guaiacol, in the presence of a catalytically effective amount of a salt of a carboxylic acid.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: September 25, 1984
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Serge Ratton
  • Patent number: 4469897
    Abstract: A method for preparing monoalkylethers of hydroquinone and of substituted hydroquinones of general formula ##STR1## in which R is an alkyl group and R.sub.1 is hydrogen or an alkyl group, wherein a hydroquinone compound of general formula ##STR2## is reacted with an alcohol or formula R-OH in the presence of transition metal salts, either in the presence or in the absence of air or oxygen.
    Type: Grant
    Filed: October 21, 1981
    Date of Patent: September 4, 1984
    Assignee: Anic S.p.A.
    Inventors: Franco Rivetti, Ugo Romano, Nicola Di Muzio
  • Patent number: 4435601
    Abstract: Optionally aldehyde substituted polyphenols are prepared by oxidizing, with hydrogen peroxide, a hydroxybenzaldehyde bearing at least one aldehyde substituent ortho- and/or para- to the nuclear hydroxyl group, in an aqueous reaction medium and in the presence of an alkali or alkaline earth metal base, the process being characterized in that the pH of the reaction medium is continuously maintained at a value no greater than 7 throughout the course of the oxidation reaction.The subject process is well suited for the preparation of, e.g., hydroxy-p-vanillin from guaiacol, and the novel compound 2,4,6-triformylphenol.
    Type: Grant
    Filed: July 7, 1981
    Date of Patent: March 6, 1984
    Assignee: Rhone-Poulenc Industries
    Inventors: Karel Formanek, Daniel Michelet, Dominique Petre
  • Patent number: 4427686
    Abstract: A compound of the formula (I): ##STR1## wherein R.sub.1 is hydrogen or C.sub.1-6 alkyl;R.sub.2, R.sub.3 and R.sub.4 are the same or different and are chosen from hydrogen, hydroxyl, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy and C.sub.1-4 alkanoyl;G is H or OH; andm and n are independently 1 to 3; with the proviso that when G is OH, one of m or n is 1; is useful in the prophylaxis and treatment of diseases whose symptoms are controlled by the mediators of the allergic response, for example asthma, hay fever, rhinitis and allergic eczema.
    Type: Grant
    Filed: December 8, 1981
    Date of Patent: January 24, 1984
    Assignee: Beecham Group Limited
    Inventors: Derek R. Buckle, Harry Smith