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Synthesis 2009(22): 3828-3832  
DOI: 10.1055/s-0029-1216992
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A New and More Efficient Synthesis of Methylene Acetals

Guobiao Chua, Yanqiao Zhanga, Chunbao Li*a, Yuqing Zhangb
a Department of Chemistry, College of Science, Tianjin University, Tianjin 300072, P. R. of China
Fax: +86(22)27403475; e-Mail: lichunbao@tju.edu.cn;
b School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, P. R. of China
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Publication History

Received 18 June 2009
Publication Date:
08 September 2009 (online)

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Shao, M.; Chu, G.; Li, C. unpublished results.