138002-08-1Relevant academic research and scientific papers
Dihydroxyacids from the chlorination of ketones: an unexpected process
Guthrie, J. Peter,Cossar, John,Lu, Jinqiao
, p. 1904 - 1908 (2007/10/02)
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. Key words: 2-phenyl glyceric acid, propiophenone, chlorination, hydrolysis, rearrangement, cycloheptanone, 1,2-dihydroxycyclohexanecarboxylic acid.
