N-halosuccinimide-mercaptoethanol cohalogenation of olefinic fatty methyl esters: Synthesis of β-halo thioethoxylates

Olefinic fatty methyl esters, undec-10-enoate (1), octadec-Z-9-enoate (2), methyl-12 hydroxy octadec-Z-9-enoate (3), on reaction with N-halosuccinimides (4,5), that is, N-bromosuccinimide (4) or N-chlorosuccinimide (5) and 2-mercaptoethanol (6) in benzene, gave β-bromo- or β-chlorothioethoxylates (8–13). β-Halothioethoxylates so formed were acetylated with acetyl chloride in CH₂Cl₂ to form the respective acetylated products (20–25).