Chalcogen Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/453)
  • Patent number: 4564479
    Abstract: Compounds of the formula I ##STR1## in which A is C.sub.2-12 -alkenyl, C.sub.4-8 -cycloalkenyl or a grouping--C(R).dbd.C(R')--Y and Y, R, R', R.sub.1, R.sub.2, R.sub.3 and R.sub.3 ' are as defined in patent claim 1, can be prepared in high yields in a simple and economical manner by reacting corresponding bromobenzenes or iodobenzenes with a compound HA in the presence of an alkali metal salt or alkaline earth metal salt of an aliphatic monocarboxylic acid having 1-12 C atoms or benzoic acid, of a cyclic or N,N-disubstituted amide as the solvent, particularly N,N-dimethylformamide, and of a palladium compound which can, if desired, contain arsenic or phosphorus, as the catalyst.
    Type: Grant
    Filed: October 29, 1982
    Date of Patent: January 14, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Alwyn Spencer
  • Patent number: 4562299
    Abstract: A process for the preparation of water-soluble vicinal diols by means of a direct catalytic hydroxylation of the corresponding olefines with H.sub.2 O.sub.2. An olefine possibly carrying functional groups inert under the reaction conditions, and whose corresponding vicinal diol is soluble in water, is made to react, under vigorous stirring, with H.sub.2 O.sub.2 at a temperature between 0.degree. and 120.degree. C. and at a pressure between 1 and 100 atmospheres, in a two-phase aqueous liquid/organic liquid system consisting or consisting essentially of an acid aqueous phase containing H.sub.2 O.sub.2 and of an organic phase containing (1) said olefine; (2) possibly a solvent immiscible with the aqueous phase; and (3) a catalyst of the formula:Q.sub.3 XW.sub.4 O.sub.24-2nwherein Q represents an onium (RR.sub.1 R.sub.2 R.sub.3 M).sup.+ cation, wherein M is chosen from among N, P, As and Sb, and R, R.sub.1, R.sub.2 and R.sub.
    Type: Grant
    Filed: December 12, 1984
    Date of Patent: December 31, 1985
    Assignee: Montedison S.p.A.
    Inventors: Carlo Venturello, Mario Gambaro
  • Patent number: 4560777
    Abstract: Process for preparing esters of 2-(6'-methoxy-2'-naphtyl)-propionic acid via rearrangement of new ketals of 2-halo-1-(6'-methoxy-2'-naphtyl)-propan-1-one in the presence of a Lewis acid.The esters thus obtained are useful as intermediate products for preparing Naproxen.The process involves the preparation of the following new compounds:ketals of 2-halo-1-(6'-methoxy-2'-naphtyl)-propan-1-oneesters of 2-(5'-bromo-6'-methoxy-2'-naphtyl)-propionic acid1-(5'-bromo-6'-methoxy-2'-naphtyl)-propan-1-one2-halo-(5'-bromo-6'-methoxy-2'-naphtyl)-propan-1-one.
    Type: Grant
    Filed: August 4, 1983
    Date of Patent: December 24, 1985
    Assignee: Blaschim S.p.A.
    Inventors: Claudio Giordano, Aldo Belli, Fulvio Uggeri, Giovanni Villa
  • Patent number: 4554364
    Abstract: It has been surprisingly discovered in accordance with the present invention that when 1,3-dioxolane is reacted with formaldehyde in the presence of tert-butyl hydroperoxide and a cobalt initiator, the reaction preferentially involves an addition of the formaldehyde to the 2-methylene group of the 1,3-dioxolane with only minor reaction with the 4-methylene and 5-methylene groups of the 1,3-dioxolane whereby the reaction product that is formed contains significant quantities of 2-hydroxyalkyl-1,3-dioxolanes and only minimal amounts of the undesired methyl formate by-product. 2-Hydroxymethyl-1,3-dioxolane is hydrolyzed with comparative ease to ethylene glycol and the corresponding glycol aldehyde (CHO--CH.sub.2 --OH). The glycol aldehyde in turn can be catalytically hydrogenated to form additional quantities of ethylene glycol.
    Type: Grant
    Filed: December 19, 1984
    Date of Patent: November 19, 1985
    Assignee: Texaco Inc.
    Inventors: John R. Sanderson, Ernest L. Yeakey, Jiang-Jen Lin
  • Patent number: 4550184
    Abstract: It has been surprisingly discovered in accordance with the present invention that when 1,3-dioxolane is reacted with formaldehyde in the presence of an organic peroxide, the reaction preferentially involves an addition of the formaldehyde to the 2-methylene group of the 1,3-dioxolane with only minor reaction with the 4-methylene and 5-methylene groups of the 1,3-dioxolane whereby the reaction product that is formed contains significant quantities of 2-hydroxymethyl-1,3-dioxolane. 2-Hydroxymethyl-1,3-dioxolane is hydrolyzed with comparative ease to ethylene glycol and the corresponding glycol aldehyde (CHO--CH.sub.2 --OH). The glycol aldehyde in turn can be catalytically hydrogenated to form additional quantities of ethylene glycol.
    Type: Grant
    Filed: December 19, 1984
    Date of Patent: October 29, 1985
    Assignee: Texaco Inc.
    Inventors: Ernest L. Yeakey, John R. Sanderson
  • Patent number: 4537980
    Abstract: A new method for the preparation of acetals of long chain fatty aliphatic aldehydes and polyols containing four or more hydroxyl groups which produces the acetals in a relatively pure form by reaction in a mutual solvent, preferably a C.sub.1 to C.sub.4 fatty carboxylic acid. The `clean` acetals are useful emulsifying agents and their esters and polyalkoxy substituents are useful dispersants and surfactants for aqueous compositions.
    Type: Grant
    Filed: December 23, 1983
    Date of Patent: August 27, 1985
    Assignee: Imperial Chemical Industries Limited
    Inventor: James N. Greenshields
  • Patent number: 4536585
    Abstract: It is disclosed that a Pd-Tl alloy catalyst is used in making acetals and acetalic ethers from alcohols and saturated or unsaturated aldehydes, and to make cyclic acetals and cyclic acetalic ethers when reacting with diols.
    Type: Grant
    Filed: December 5, 1983
    Date of Patent: August 20, 1985
    Assignee: The Standard Oil Company
    Inventors: Christos Paparizos, Robert S. Shout, Wilfrid G. Shaw
  • Patent number: 4518784
    Abstract: There is presented a process for the manufacture of hexahydronaphthacene derivatives of the general formula ##STR1## wherein one of R.sup.1 and R.sup.2 represents a hydrogen atom and the other represents a hydrogen atom or a hydroxy group of R.sup.1 and R.sup.2 together represent a protected oxo group, R.sup.3 represents a hydrogen atom or a hydroxy or acyloxy group and R.sup.4 represents a lower alkyl or esterified carboxy group or a group of the formula ##STR2## wherein R.sup.5 and R.sup.6 together form an oxo group or a protected oxo group and X represents a hydrogen atom or a hydroxy or acyloxy group or ##STR3## in which n stands for 1 or 2 and Y represents a hydrogen atom or an alkyl or acyl group.Also presented are certain of the novel derivatives per se and various novel intermediates in the process.
    Type: Grant
    Filed: February 23, 1984
    Date of Patent: May 21, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael J. Broadhurst, Cedric H. Hassall, Gareth J. Thomas
  • Patent number: 4518785
    Abstract: Novel malondialdehyde tetraalkylacetals and the preparation of malondialdehyde tetraalkylacetals by reacting alkyl formates, oxiranes and alkyl vinyl ethers in the presence of a halide of boron, antimony(V), iron(III), tin(II or IV) and/or zinc.The malondialdehyde tetraalkylacetals obtainable by the process of the invention are valuable starting materials for the preparation of dyes, pest control agents and pharmaceuticals.
    Type: Grant
    Filed: October 29, 1982
    Date of Patent: May 21, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Eckhardt, Klaus Halbritter, Wolfgang Rohr
  • Patent number: 4515969
    Abstract: There is presented a process for the manufacture of hexahydronaphthacene derivatives of the general formula ##STR1## wherein one of R.sup.1 and R.sup.2 represents a hydrogen atom and the other represents a hydrogen atom or a hydroxy group or R.sup.1 and R.sup.2 together represent a protected oxo group, R.sup.3 represents a hydrogen atom or a hydroxy or acyloxy group and R.sup.4 represents a lower alkyl or esterified carboxy group or a group of the formula ##STR2## wherein R.sup.5 and R.sup.6 together form an oxo group or a protected oxo group and X represents a hydrogen atom or a hydroxy or acyloxy group or ##STR3## in which n stands for 1 or 2 and Y represents a hydrogen atom or an alkyl or acyl group.Also presented are certain of the novel derivatives per se and various novel intermediates in the process.
    Type: Grant
    Filed: January 23, 1984
    Date of Patent: May 7, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael J. Broadhurst, Cedric H. Hassall, Gareth J. Thomas
  • Patent number: 4493846
    Abstract: A compound of the formula ##STR1## wherein X.sup.1 is a free or esterified carboxyl group, a hydroxymethyl group, a cyano group, a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7-membered saturated heterocyclic group) or a group of the formula: ##STR3## (R.sup.a and R.sup.b are each as defined above), Y is an ethylene group or a vinylene group, R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sub.1 and R.sub.2, when taken together, means a single linkage to form a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.
    Type: Grant
    Filed: March 13, 1981
    Date of Patent: January 15, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Ono, Akihiko Sugie, Hajime Kawakami, Shunsuke Sami, Atsuyuki Kojima, Junki Katsube
  • Patent number: 4471139
    Abstract: Processes for preparing isomerically pure 3-methylthiophene-2-carboxaldehyde, an intermediate for synthesis of anthelmintic agents, by reaction of mercaptoacetaldehyde or the dimer, or a polymer thereof, or a dialkylacetal thereof in the presence of a base with (1) methyl vinyl ketone or an alpha- or beta-oxidized derivative of methyl vinyl ketone to form a 3-oxobutylmercaptoacetaldehyde or dialkyl acetal thereof, or an alpha- or beta-substituted derivative thereof which is then converted to 3-methylthiophene-2-carboxaldehyde via appropriate steps including, if necessary, treatment with acid, followed, if necessary, by enamine catalyzed cyclization and, in the case of using methyl vinyl ketone as reactant, a dehydrogenation step; or (2) 3-butyn-2-one to produce a mixture of isomeric 3-oxobut-1-enylmercaptoacetaldehyde or dialkyl acetals thereof which is cyclized to 3-methylthiophene-2-carboxaldehyde.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: September 11, 1984
    Assignee: Pfizer Inc.
    Inventor: Glenn C. Andrews
  • Patent number: 4465866
    Abstract: Some 4-(2'-hydroxy-3'-alkoxy)propoxymethyl-1,3-dioxolanes are prepared by reacting alkylglycidyl ethers with acetal or ketal derivatives of glycerol in the presence of an acidic or basic catalyst. Also disclosed is a process for preparing certain 2-hydroxy-3-alkoxy-propylglyceryl ethers, which process comprises subjecting the 4-(2'-hydroxy-3'-alkoxy)propoxymethyl-1,3-dioxolanes to hydrolysis. The above processes can afford intended reaction products with good yield without need for any special post-reaction treatment.
    Type: Grant
    Filed: May 5, 1982
    Date of Patent: August 14, 1984
    Assignee: Kao Soap Co., Ltd.
    Inventors: Naotake Takaishi, Kouichi Urata, Yoshiaki Inamoto
  • Patent number: 4465869
    Abstract: The specification describes a process for the production of a 4-alkoxymethyl-1,3-dioxolan in good yield, in high purity and in a simple manner by reacting an alkyl glycidyl ether with a carbonyl compound in the presence of an acid catalyst. The 4-alkoxymethyl-1,3-dioxolan is useful as an intermediate for the production of an .alpha.-monoalkyl glyceryl ether by hydrolysis.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: August 14, 1984
    Assignee: Kao Corporation
    Inventors: Naotake Takaishi, Kouichi Urata, Yoshiaki Inamoto
  • Patent number: 4459418
    Abstract: A new method for the preparation of acetals of long chain fatty aliphatic aldehydes and polyols containing four or more hydroxyl groups which produces the acetals in a relatively pure form by reaction in a mutual solvent, preferably a C.sub.1 to C.sub.4 fatty carboxylic acid. The `clean` acetals are useful emulsifying agents and their esters and polyalkoxy substituents are useful dispersants and surfactants for aqueous compositions.
    Type: Grant
    Filed: April 15, 1980
    Date of Patent: July 10, 1984
    Assignee: Imperial Chemical Industries
    Inventor: James N. Greenshields
  • Patent number: 4423071
    Abstract: Mono-, di-, tri- and tetra-esters derived from an acid of the general formula:R--OHin which R represents an acyl radical of the general formula: ##STR1## in which n represents 0 or 1, m represents 0, 1, 2, 3 or 4, R.sub.1 and R.sub.2 each represent a straight- or branched-chain alkyl radical having from 1 to 5 carbon atoms, R.sub.3 represents hydrogen or a straight- or branched-chain alkyl radical having from 1 to 5 carbon atoms, the sum of the carbon atoms in R.sub.1 and R.sub.2 being from 4 to 10 when R.sub.3 represents hydrogen and the sum of the carbon atoms in R.sub.1, R.sub.2 and R.sub.3 being from 6 to 15 when R.sub.3 is different from hydrogen, or R.sub.1 and R.sub.2 when they are taken together represent a tetramethylene, pentamethylene or hexamethylene radical and R.sub.
    Type: Grant
    Filed: March 3, 1980
    Date of Patent: December 27, 1983
    Assignee: Sanofi
    Inventors: Michel Chignac, Claude Grain, Fernand Jammot, Charles Pigerol, Pierre Eymard, Bernard Ferrandes
  • Patent number: 4413142
    Abstract: L-carnitine is prepared by a synthesizing process starting from D-mannitol. The synthesis is started with the formation of a D-mannitol ketonide (more specifically D-mannitol acetonide from D-mannitol and acetone, whereafter the D-mannitol is split by oxidation to give glyceraldehyde acetonide, which is further reduced to glycerol acetonide. Then the free hydroxyl group is exchanged with a halogen atom (chlorine) with the formation of chlorodihydroxy propane, the primary alcoholic group of which is functionalized with the acid chloride of a sulfonic acid (tosylchloride). The reaction of the tosyl derivative with the salt of hydrogen cyanide leads to the formation of the corresponding nitrile which, when reacted with trimethylamine gives carnitinonitrile. The nitrile group is now hydrolyzed to give L-carnitine chloride. The formation of L-carnitine can then be obtained by exchanging the chloride ion with a hydroxyl ion.
    Type: Grant
    Filed: March 15, 1982
    Date of Patent: November 1, 1983
    Assignee: Anic S.p.A.
    Inventors: Mario Fiorini, Claudio Valentini
  • Patent number: 4390707
    Abstract: A method for the preparation of cyclopentenones of the general formula (VIII): ##STR1## wherein n is 5-7, has been developed which proceeds via the acid catalyzed deprotection and rearrangement of novel substituted-.alpha.-hydroxymethylfurans of general formula (VII): ##STR2## wherein R is a hydroxyl protecting group, R.sub.1 and R.sub.2 are methyl or ethyl or together form --(CH.sub.2).sub.3 -- and n is as above described. Cyclopentenones of formula VIII are useful intermediates in prostaglandin analog synthesis.
    Type: Grant
    Filed: February 2, 1982
    Date of Patent: June 28, 1983
    Assignee: American Cyanamid Company
    Inventor: Steven L. Peake
  • Patent number: 4388161
    Abstract: Bright deposits of tin and tin/lead alloys by electrocoating are obtained by using a bath containing tin salts and, optionally, lead salts, aldehydes and/or ketones as brighteners as well as surfactants besides sulfuric acid and/or borofluohydric acid wherein part or all of the aldehydes and/or ketones are replaced by a cyclic reaction product of one or more aromatic aldehydes and epihalohydrin of the general formula ##STR1## (Hal being chlorine or bromine, R being a phenyl, naphthyl or pyridyl radical which is optionally substituted by one to three members of the group consisting of chlorine, bromine or fluorine atoms, alkyl or alkoxy groups having 1 to 3 carbon atoms, carboxy and hydroxy groups). Preferably the cyclic reaction product is contained in the bath in an amount of from 0.1 to 2 g/liter of the bath.
    Type: Grant
    Filed: June 24, 1982
    Date of Patent: June 14, 1983
    Assignee: Elektro-Brite GmbH & Co. KG
    Inventors: Simeon Acimovic, Karl-Heinz Lindemann, Volker G. Kunz
  • Patent number: 4374999
    Abstract: Acrolein acetals are selectively hydroformylated on the unsaturated carbon atom adjacent to the carbon bearing two ether groups in the presence of a supported rhodium-cobalt bimetallic cluster. The resulting internally hydroformylated product is useful as a precursor of methacrylic acid.
    Type: Grant
    Filed: January 2, 1981
    Date of Patent: February 22, 1983
    Assignee: The Dow Chemical Company
    Inventor: Philip E. Garrou
  • Patent number: 4360694
    Abstract: The object of the present invention is a novel and simple process for the production of 1,2-diacyl-sn-glycerols, wherein the acyl groups may be the same or different. According to the invention D-mannitol is reacted with benzene boronic acid or a derivative thereof to form a D-mannitol-monobenzeneboronate which compound is acylated either to form, after removal of the benzeneboronate protective group, a 1,2,5,6-tetraacyl-D-mannitol with four identical acyl groups, or is acylated selectively in two stages, by first acylating the 1,6-hydroxy groups of the boronate protected D-mannitol to form, after removal of the boronate protection, a 1,6-diacyl-D-mannitol, which then is repeatedly reacted with a benzene boronic acid or a derivative thereof and then acylated in the 2- and 5-positions.
    Type: Grant
    Filed: April 6, 1981
    Date of Patent: November 23, 1982
    Assignee: KSV-Chemicals Oy
    Inventors: Paavo K. J. Kinnunen, Tom M. Schroder, Jorma A. Virtanen