Interaction of Thionyl Chloride and Hydroxy Compounds

Abstract

Human and Mills¹ have generalized the procedure of Carré and Libermann², who prepared, by adding an equimolecular amount of pyridine, the chlorides of the few acids which until then had withstood the action of thionyl chloride. Gerrard and French³ found it unnecessary to use an equimolecular amount of pyridine in the interaction of thionyl chloride and hydroxy compounds, and proposed to modify the Darzens' procedure⁴ by adding the thionyl chloride to a hydroxy compound with a few drops of a tertiary base, and heating for four hours at 65–80° C., which gives them the corresponding chloride.