Synthesis of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone, a potent mutagen

Abstract

Starting from tetrachloroacetone 1 and (carbomethoxymethylene)triphenylphosphorane 4, the title compound 16 was prepared in five steps in 44% yield. Spectroscopic and chromatographic data indicated that this material was identical to a potent mutagen isolated from kraft pulp chlorination effluent. Various mutant Salmonellatyphimurium strains (TA 98, 100, and 1537) behaved similarly when incubated with either 16 or the isolated mutagen.