Formation and the Synthesis of 2, 3, 5, 6-Tetrachlorophenylacetic Acid.

Abstract

2, 3, 5, 6-Tetrachloroaniline was diazotized in a mixture of acetic acid and sulfuricacid according to the conventional procedures. The diazonium solution was then added dropwise into 700% sulfuric acid at 150-160°C, and the products were steamdistilled as soon as they were formed. Upon purification of the solids in the distillate, a small amount of colorless crystals (mp 212-213°C) showing a marked biological activity was obtained. This substance proved to be a new compound, 2, 3, 5, 6-tetrachlorophenylacetic acid. In the light of the fact that diazonium compounds usually decompose into phenols via diazonium ions, it is of interest to note that 2, 3, 5, 6-tetrachlorophenylacetic acid was obtained instead of 2, 3, 5. 6-tetrachlorophenol.