Hoechst Celanese Corporation

Other

Basf Corporation

Varadaraj Elango

Kenneth G Davenport

Werner H Mueller

Frank B Gupton

John C Saukaitis

John R Fritch

Michael P Bodman

Donald R Larkin

Mohammad Aslam

Brad L Smith

Edward G Zey

Graham N Mott

Mark A Murphy

William R Lee

Gary L Moss

Cheryl A Littau

Rajagopal Sakamuri

Jeffrey S Hurley

A method is provided for the preparation of alpha-aryl-propionic acids such as ibuprofen by carbonylating the corresponding 1-arylethyl halide in an acidic aqueous medium containing a palladium catalyst. In the preparation of ibuprofen, 1-(4&prime;-isobutylphenyl)ethyl halide is reacted with carbon monoxide in an acidic aqueous medium containing a palladium catalyst.

Process for the carbonylation of arylalkyl halides

A process for preparing bis alkylene glycol esters of an alkali metal salt of 5-sulfoisophthalic acid. The subject compound is useful in preparing modified polyesters which can be dyed with basic or cationic dyes. The process is economical and low cost since intermediate reaction products are not purified.

Process for glycol esters of an alkali metal salt of 5-sulfoisophthalic

A new process for the manufacture of 1,3-cyclohexanedione is disclosed wherein a selected resorcinol is reduced with a hydrogen donor in the presence of a metal catalyst to produce a product which is then neutralized with an acid.

Process for the manufacture of 1, 3-cyclohexanedione

The present invention pertains to a method of preparing substituted and unsubstituted N-hydroxy-2-aminobutane diacid derivatives which can be dehydrated to 2-aminobut-2-ene dioic acid derivatives, which can be subsequently converted to pyridine and quinoline derivatives.

Process for preparing pyridine and quinoline derivatives

The present invention pertains to a method of preparing substituted and unsubstituted N-hydroxy-2-aminobutane diacid derivatives. The invention also pertains to the use of N-hydroxy-2-aminoethane derivatives (including the N-hydroxy-2-aminobutane diacid derivatives) in the preparation of pyridine derivatives.

Process for preparing pyridinecarboxylic acid derivatives

This invention discloses a novel process for preparing cinnamic acid derivatives. The inventive process is illustrated by the synthesis of 2-ethylhexyl p-methoxycinnamate by coupling p-methoxybenzenediazonium tetrafluoroborate with 2-ethylhexyl acrylate in an alcohol solution, wherein a buffer compound such as sodium acetate is present, the coupling reaction being catalyzed by a mixture comprising a copper salt, such as cuprous chloride, and a palladium salt, such as Li.sub.2 PdCl.sub.4.

Process for synthesizing substituted cinnamic acid derivatives

A method for synthesizing 2-(4-amidophenoxy)alkanoic acids and esters and 2-(4-aminophenoxy)alkanoic acids and esters by reacting a hydroxyaromatic ketone derivative with a 2-substituted alkanoic acid or ester under basic conditions and thereafter reacting with a hydroxylamine derivative and conducting a Beckmann Rearrangement with subsequent solvolysis.

Synthesis of 2-(4'-aminophenyloxy) alkanoic acids & acids & esters &

An intermediate for the manufacture of nabumetone, 4-(6'-methoxy-2'-naphthyl)-3-buten-2-one, is prepared by contacting 2-bromo-6-methoxynaphphalene with methyl vinyl ketone in the presence of a palladium catalyst at from about 50.degree. C. to about 200.degree. C. for a time sufficient to cause substantially complete reaction to occur.

Preparation of 4-(6'-methoxy-2'-naphthyl)-3-buten-2-one

A process for the preparation of 2,2-diorgano-3-arylpropionic acids is disclosed by the carbonylation of corresponding 2,2-diorgano-1-aryl ethanol in the presence of a Lewis acid catalyst. Furthermore, a process for the production of 2,2-diorgano-3-arylpropionic esters is disclosed by reacting a corresponding 2,2-diorgano-1-aryl ethanol with carbon monoxide and an alcohol in the presence of a Lewis acid catalyst.

Preparation of 2,2-diorgano-3-arylpropionic acids and esters thereof

A method is provided for the production of 2,2-diorgano-1-indanones, e.g., 2,2-dimethyl-1-indanone, by reacting an alcohol which is the corresponding (diorganosubstitutedmethyl)phenyl(or substitutedphenyl)carbinol, e.g., 2-methyl-1-phenyl-1-propanol, with carbon monoxide in the presence of a Lewis acid catalyst, e.g., hydrogen fluoride, with any substituents on the phenyl group of the alcohol being hydroxy or organo. The foregoing reaction is preferably integrated with the preparation of the feed alcohol by reducing the corresponding (diorganosubstitutedmethyl)phenyl(or substitutedphenyl)ketone, e.g., isobutyrophenone, with a reducing agent containing available hydrogen, e.g., sodium borohydride, or with hydrogen gas in the presence of a hydrogenation catalyst.

Method for producing 1-indanone derivatives

A method for synthesizing 2-(4-hydroxyphenoxy)alkanoic acid esters by reacting a hydroxyaromatic ketone derivative with a 2-substituted alkanoic acid ester under basic conditions and thereafter oxidizing the intermediate with subsequent hydrolysis.

Synthesis of 2-(4-hydroxyphenoxy) alkanoic acid esters

A method is provided for the preparation of ibuprofen by carbonylating 1-(4'-isobutylphenyl)ethanol (IBPE) with carbon monoxide in an acidic aqueous medium, e.g. containing at least 10% of water based on the weight of IBPE initially added, at a temperature of at least about 10.degree. C. and a carbon monoxide pressure of at least about 500 psig, and in the presence of (1) a catalyst complex consisting essentially of a palladium compound in which the palladium has a valence of zero to 2 and is complexed with at least one monodentate phosphine ligand miscible with the organic phase of the reaction medium, the phosphorus/palladium mole ratio in said palladium compound and ligand being at least about 2:1 when the palladium/IBPE mole ratio is such that palladium=1 and IBPE=10,000 or more; (2) dissociated hydrogen ions from an acid which is substantially completely ionizable in dilute aqueous solution such that the mole ratio of hydrogen ions to IBPE added to the reaction zone is at least about 0.15; and, (3) dissociated halide ions such that the mole ratio of halide ions to IBPE added to the reaction zone is at least about 0.15. Advantageously, a hydrogen halide is the source of hydrogen ions and halide ions. The carbonylation is preferably integrated with a method of producing IBPE from isobutylbenzene wherein the latter compound is subjected to Friedel-Crafts reaction with an acetylating agent to produce 4-isobutylacetophenone, which is then reduced with hydrogen in the presence of a hydrogenation catalyst, or with a reducing agent containing available hydrogen, to obtain IBPE. The palladium catalyst complex can be precipitated from an organic phase of the carbonylation reaction which typically includes the ibuprofen product. The precipitated catalyst complex can be recycled without further treatment.

Method for producing ibuprofen

A method for synthesizing 2-(4-hydroxyphenoxy)alkanoic acids by reacting a hydroxyaromatic ketone derivative with a 2-substituted alkanoic acid under basic conditions and thereafter oxidizing the intermediate with subsequent hydrolysis.

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Corpus Christi, TX, United States of America

Varadaraj Elango