THE ACTION OF HYPOCHLOROUS ACID ON ARYLIDENECYANOACETIC ACIDS

Abstract

The action of hypochlorous acid on p-methoxybenzylidenecyanoacetic acid has been found to produce p-methoxyphenylacetic acid. When treated in the same way, o-methoxybenzylidene-, veratrylidene- and piperonylidenecyanoacetic acids give the corresponding substituted phenylacetic acids in moderately good yields. Several schemes suggesting how this transformation may occur are advanced.o-Chlorobenzylidenecyanoacetic acid gives α-cyano-β-(2-chlorophenyl)glycidic acid but this substance could not be converted to o-chlorophenylacetic acid. Less definite results were obtained when the aryl group of the original acid was phenyl, o- and m-nitrophenyl, cinnamyl, furyl, 3-nitroanisyl and 6-nitropiperonyl.o-Chlorobenzylidene-, o-methoxybenzylidene-, 3-nitroanisylidene-, and 6-nitropiperonylidenecyanoacetic acids have been prepared for the first time.