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).
Catalyst recovery procedures enabling recycle of catalyst residues and
efficient recovery of amine hydrogen halide scavenger and solvent used in
the arylation reaction are described, as well as novel, highly efficient
methods of conducting the carbonylation reaction. The technology is
economical and suitable for use on an industrial 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.