Dihydroxyacids from the chlorination of ketones: an unexpected process

Abstract

. Can. J. Chem. 69, 1904Chem. 69, (1991. Chlorination of propiophenone in aqueous alkali at room temperature, with low concentrations of hypochlorite, leads to 2-phenylglyceric acid as the major product. This acid is formed by further oxidation of 1-phenyl-1,2-propanedione, which is an intermediate in the oxidation of propiophenone. Formation of this acid is reasonable in the light of other halogenation chemistry. Analogous reactions are observed for butyrophenone, which yields 2,3-dihydroxy-2-phenylbutanoic acid, and for cycloheptanone, which yields 1,2-dihydroxycyclohexanecarboxylic acid.