Oxidation of o-hydroxy arylketones N-acylhydrazones with sodium hypochlorite

ORGN 137

Antigoni Kotali, kotali@eng.auth.gr and Ioannis S. Lafazanis. Department of Chemical Engineering, University of Thessaloniki, Thessaloniki, 54124, Greece
Oxidation of o-hydroxy acetophenone N-benzoylhydrazone with sodium hypochlorite leads to the formation of 1-acetyl-2-benzoylbenzene in good yield. The synthetic scheme which is shown below involves a two step transformation of phenolic hydroxy to an acyl group. The same product is obtained almost quantitatively when either lead tetraacetate or diacetoxyiodobenze is used as alternative oxidant. However, sodium hypochlorite has the advantages of being less toxic and costly. The generality of this reaction as well as the optimisation of the yield will be further investigated.