The Chlorination of 4-Methylbenzene-1,2-diamine: the Formation of 2,3,4,5,5-Pentachloro-6,6-dihydroxy-4-methylcyclohex-2-enone Hydrate and Some Transformation Products

Abstract

Chlorination of 4-methylbenzene-1,2-diamine gives the pentachloro ketone (3) which, on treatment with base, is converted mainly into the hydroxy acid (4). Methylated derivatives (5) and (6), and an unexpected transformation product of the hydroxy acid (4) are described. The chlorination of tetrachlorocatechol (8) gives the hexachloro ketone (9). X-Ray crystal structure determinations are reported for compounds (3)-(7) and (9).