Abstract:
The purpose of this study was to investigate the Wolff-Kishner and Clemmensen reduction of 1,3-dihydroxyacetone in order to convert carbonyl group to methylene group. Wolff-Kishner reduction was carried out on 1,3-dihydroxyacetone by oximation followed by reductive deoximation of 1,3-dihydroxyacetone oxime in the presence of base. It was observed that 1,3-propanediol was not obtained due to unexpected formation of an intermediate 3,3,6,6-tetrahydroxymethyl-1,2,4,5-tetrazinane which was decomposed at 120 °C. Clemmensen reduction of 1,3-dihydroxyacetone was carried out. Surprisingly, it gave lactic acid in 84 %yield instead of the expected 1,3-propanediol. The mechanism of transformation from 1,3-dihydroxyacetone to lactic acid took place via keto-enol tautomerization and followed by proton transfer from solvent. The mechanism was proposed and supported by the reaction in D2O in which deuterium atom was incorporated into methyl group of lactic acid.
