A New and More Efficient Synthesis of Methylene Acetals

Abstract

A new and efficient synthesis of benzyl chlorides and methylene acetals by use of 2,4-dichloro-6-methoxy[1,3,5]triazine (MeOTCT) and dimethyl sulfoxide has been developed. Chlorides are the major products for benzyl alcohols, while methylene acetals are the major products for secondary alcohols. This procedure provides the highest yields so far for methylene acetals of steroids. A plausible mechanism is proposed on the basis of the experiments.

Key words

2,4-dichloro-6-methoxy[1,3,5]triazine - dimethyl sulf­oxide - alcohols - benzyl chlorides - methylene acetals

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12

Shao, M.; Chu, G.; Li, C. unpublished results.