Syntheses of Alkyl 3-Chloro-2-hydroxypropyl Sulfides via Sulfonium Salts Obtained from Alkyl 2-Cyanoethyl Sulfides and 1-Chloro-2, 3-epoxypropane

Abstract

Alkyl 2-cyanoethyl sulfides [2] were prepared by the reactions of mercaptans with acrylonitrile with the aid of Triton B. The reactions of [2] with 1-chloro-2, 3-epoxypropane in the presence of aq. HClO4 (60%) led to aqueous solutions of alkyl(3-chloro-2-hydroxypropyl)(2-cyanoethyl)sulfonium prechlorates [3].The additions of aq. NaHCO3 to the above solutions caused the Hofmann Degradation of [3], and afforded alkyl 3-chloro-2-hydroxypropyl sulfides [4] in good yields.
Further, bis(3-chloro-2-hydroxypropyl)sulfide [6], which can be one of starting materials of epoxy resins containing sulfur atom, was also synthesized bythis method.