A New Synthesis of Arylacetic Esters Starting from Aromatic Aldehyde by the Use of Methyl (Methylthio)methyl Sulfoxide
- 1 July 1979
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 52 (7) , 2013-2022
- https://doi.org/10.1246/bcsj.52.2013
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.This publication has 7 references indexed in Scilit:
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