Influence of Tertiary Bases on the Interaction of Thionyl Chloride and Hydroxy Compounds

Abstract

IN contrast to the observations of Human and Mills¹ on the use of pyridine in the interaction of thionyl chloride and the carboxylic group, we found that instead of one molecular proportion of tertiary base in the Darzens' procedure² for hydroxy compounds, much less than 0·1 mol. of base or its hydrochloride was sufficient. Thionyl chloride (1·0 mol.) was added to a cooled mixture of the hydroxy compound (iso-amyl, n-butyl, Î-phenylethyl alcohols, or ethyl lactate) (1·0 mol.), and a few drops of base (pyridine, quinoline, or dimethylaniline) or a small amount of the corresponding hydrochloride. An excellent yield of the chloride (RC1) was distilled directly from the reaction mixture, after it had been heated for four hours at 65–80° (depending on the base). Yields approaching 95 per cent were obtained.