Synthetic Approaches to Chlorinated 5-Hydroxy-5-Methyl-2-Furanones

Article abstract of DOI:10.1016/S0040-4020(01)80248-9

The syntheses of chlorinated 5-hydroxy-furanones with a mono-, di-, and trichloromethyl group at C-5 are described.The 5-chloromethyl hydroxyfuranones were obtained by chlorination of levulinic acid followed by triethylamine promoted elimination of hydrogen chloride.Hydrolyses of chlorinated 4-cyclopentene-1,3-diones yielded 5-dichloromethyl hydroxyfuranones.The trichloromethyl group was incorporated to maleic anhydride through thermal decomposition of sodium trichloroacetate.