Preparation of carboxylic compounds and their derivatives

Details Preparation of carboxylic compounds and their derivatives Preparation of carboxylic compounds and their derivatives

C - Chemistry, Metallurgy

07

C

C07C 51/14 (2006.01) C07C 57/30 (2006.01) C07C 59/64 (2006.01) C07C 59/68 (2006.01) C07C 59/84 (2006.01) C07C 67/38 (2006.01)

Patent

CA 2336115

Palladium-catalyzed arylation of an olefin (e.g., ethylene) with an aromatic halide (e.g., 2-bromo-6-methoxynaphthalene, m-bromobenzophenone, or 4-isobutyl- 1-bromobenzene) is conducted in specified media. After a special acid or base phase separation procedure, palladium-catalyzed carbonylation of the olefinically-substituted aromatic intermediate is conducted in specified media using CO and water or an alcohol to form arylalkylcarboxylic acid or ester or substituted arylalkylcarboxylic acid or ester (e.g., racemic 2-(6-methoxy-2- naphthyl)propionic acid, 2-(3-benzoylphenyl)propionic acid, or 2-(4- isobutylphenyl)propionic acid). The technology is economical and suitable for use on an insdustrial scale whereby reaction mixtures can be efficiently separated into the desired component mixtures without need for excessive capital investment or tedious, time-consuming operations. High yields of high purity products can be achieved.

L'arylation catalysée par palladium d'une oléfine (par exemple éthylène) avec un halogénure aromatique (par exemple, 2-bromo-6-méthoxynaphtalène, m-bromobenzophénone, ou 4-isobutyl-1-bromobenzène est exécutée dans des milieux spécifiés. Après une procédure spéciale de séparation des phases d'acide ou de base, la carbonylation catalysée au palladium de l'intermédiaire aromatique à substitution oléfinique est exécutée dans des milieux spécifiés à l'aide de CO et d'eau ou d'un alcool pour former un acide ou un ester arylalkyle carboxylique ou un acide arylalkylcarboxylique ou un ester substitué (par exemple, acide racémique 2 (6-méthoxy-2-naphtyle) propionique, acide 2-(3-benzoylphényl) propionique ou acide 2 (4-isobutylphényle) proprionique. La technologie est économique et adaptée à une utilisation à l'échelle industrielle de manière à pouvoir séparer efficacement des mélanges réactionnels en mélanges de constituants voulus sans investissement excessif de capital ni opérations difficiles et interminables. On a pu obtenir des rendements élevés de produits de grande pureté.

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