[Microbial degradation and 4-chlorophenylacetic acid. Chemical synthesis of 3-chloro-4-hydroxy-, 4-chloro-3-hydroxy- and 4-chloro-2-hydroxyphenylacetic acid (author's transl)].

Pseudomonas spec. CBS 3 converts 4-chlorophenylacetic acid partly into 3-chloro-4-hydroxy-, 4-chloro-3-hydroxy-, and 4-chloro-2-hydroxyphenylacetic acid by the action of monooxygenases. However, these compounds are not intermediates in the degradation of 4-chlorophenylacetic acid. Pseudomonas spec. CBS 3 is not able to grow with 3-chloro-4-hydroxy- and 4-chloro-3-hydroxyphenylacetic acid as sole carbon source. 4-Chloro-2-hydroxyphenylacetic acid is slowly degraded forming 4-chloro-2,3-dihydroxyphenylacetic acid. The actual degradation of 4-chlorophenylacetic acid seems to be initiated by the attack of a dioxygenase. The syntheses of 4-chloro-3-hydroxyphenylacetic acid and of 4-chloro-2-hydroxyphenylacetic acid are described.