Synthesis of 2-Trifluoromethyl-1,3-cyclopentanedione and 2-Trifluoromethyl-1,4-benzoquinone via Chlorous Acid Oxidation of 3-Trifluoromethylphenol

Abstract

A new synthesis of 2-trifluoromethyl-1,4-benzoquinone and 2-chloro-2-trifluoromethyl-1,3-cyclopentanedione by oxidation of 3-trifluoromethyl-phenol with sodium chlorite/sulfuric acid (chlorous acid) is described. In addition, the hydrodechlorination of 2-chloro-2-trifluoromethyl-1,3-cyclopentanedione to give 2-trifluoromethyl-1,3-cyclopentanedione by hydroiodic acid (generated in catalytic amounts from iodine and thiophenol) has been achieved.