Preparation of Hydroxyphenylalkanoic Acids by the Willgerodt Reaction

Abstract

Hydroxyphenyl methyl and ethyl ketones were treated with ammonium polysulfide (Willgerodt reaction) to yield hydroxyphenylacetamides and β-(p-hydroxyphenyl)-propionamide, respectively, in good yields. On hydrolysis, the amides yielded the corresponding acids. A procedure suitable for large scale production of p-hydroxyphenylacetic acid was developed. © 1946, American Chemical Society. All rights reserved.