Arylacetic Esters Research Articles

A New Synthesis of Arylacetic Esters Starting from Aromatic Aldehyde by the Use of Methyl (Methylthio)methyl Sulfoxide

Abstract Methyl (methylthio) methyl sulfoxide was found to react with benzaldehyde in the presence of benzyl tri-methylammonium hydroxide (Triton B), sodium hydroxide, or potassium hydroxide, affording 1-(methylsulfinyl)1-(methylthio)-2-phenylethylene. Treatment of this product with hydrogen chloride in an alcohol gave the corresponding alkyl phenylacetate in high yield. The whole reaction sequence provides a new method for synthesizing phenylacetic esters starting from benzaldehyde. In a similar manner, (alkoxy-, halogen-, or alkyl-substituted phenyl)acetic esters could be synthesized from the corresponding aromatic aldehydes. The present method was shown to be also applicable to the production of (2-thienyl)acetic esters.

Biochemical characterization of an aryl acetic ester hydrolase isolated from human monocytes.

A carboxylic-ester hydrolase was isolated from the leukocytes of a patient with myelomonocytic leukemia. Its relative molecular mass as estimated by sucrose density-gradient sedimentation is about 70 000. The purified enzyme is specific for acetyl esters of aromatic alcohols. It is inhibited by fluoride, but insensitive to eserine or p-chloromercuriphenylsulfonate. Hydrolysis of 1-naphthyl acetate was optimal above pH 6.0; of o-nitrophenyl acetate, above 8.0. The common catalytic site for the two types of substrates on the enzyme was confirmed by competitive inhibition data.

Alkylation of arylacetic esters by phase-transfer catalysis and sodium hydride: activation and stereochemical effects of the chromium tricarbonyl group

Alkylation of arylacetic esters by phase-transfer catalysis and sodium hydride: activation and stereochemical effects of the chromium tricarbonyl group