Acylation. Part XIX. Equilibria and acetylation in the system diacetyl sulphide–hydrogen chloride–acetic acid

Abstract

Diacetyl sulphide is relatively stable in acetic acid solution. Addition of hydrogen chloride to the solution rapidly and quantitatively converts the sulphide into acetyl chloride and thiolacetic acid. In the absence of added hydrogen chloride, diacetyl sulphide acylates 2-naphthol faster than does a comparable concentration of acetic anhydride. In the presence of hydrogen chloride the major route of the acylation is through acetyl chloride, this compound being ca. 15-fold more reactive than diacetyl sulphide towards 2-naphthol at 40°.