Synthesis and Properties of Halohydroxyacetones and Halomethylglyoxals

Article abstract of DOI:10.1021/jo00133a023

A short, high-yield synthetic scheme for the preparation of halohydroxyacetones (4) and halomethylglyoxals (6) from the corresponding 3-halopyruvic acids is described.The key intermediate to both classes is the dimethyl ketal (3) of the halohydroxyacetone (4).The ketal alkohol (3) may be hydrolyzed to 4 or oxidized to the corresponding aldehyde (5) which, in turn, may be hydrolyzed to the halomethylglyoxal (6).Halohydroxyacetones (4) exist in solution as an equilibrium mixture of the free ketone and hydrate.Halomethylglyoxals (6) occur nearly exclusively as the dihydrates species.Some other properties of these compounds are described.