m-Chloroperbenzoic acid → 1-(10,10-Dioxophenoxathiin-2-yl)ethanone

Participants

Reaction Steps

To a solution of 2-acetyl phenoxathiin (J.A.C.S. 1936, 58, 717) (484 mg, 2 mmol) in methylene chloride (25 mL) there was added 85% m-chloroperoxy benzoic acid (MCPBA 1.015 g, 5 mmol) and the mixture stirred at room temperature. After 3 hours, more MCPBA was added (250 mg) and stirring was continued for a further hour. Enough methylene chloride was added to dissolve the solids, followed by calcium hydroxide (3 g); after stirring for a further 5 minutes, the mixture was filtered and the filtrate evaporated to a solid residue which was triturated with ether (10 mL) and filtered to afford the sulfone (415 mg) as a white solid, m.p.: 163°-165° C.

Provenance & Evidence