One-flask preparation of symmetrical ketones and 1,2-diketones from esters

Article abstract of DOI:10.1055/s-1991-28415

A convenient one-flask preparation of a series of symmetrical 1,2-diketones from esters is reported using sodium metal induced acyloin condensation followed by reaction with thionyl chloride. Symmetrical monoketones were obtained when after initial acyloin condensation, the reaction mixture is oxidized with aqueous sodium bromate and then reacted with thionyl chloride. Preparative aspects, the scope of the reaction, and the suggested mechanism are discussed.