2013•The Journal of Organic ChemistryRequires access

Methylene Acetal Formation from 1,2- and 1,3-Diols Using an O,S-Acetal, 1,3-Dibromo-5,5-dimethylhydantoin, and BHT

Tomohiro Maegawa, Yasuyuki Koutani, Kazuki Otake, Hiromichi Fujioka

Abstract

A mild and efficient method for formation of methylene acetals from 1,2- and 1,3-diols using methoxymethylphenylsulfide, 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), and dibutylhydroxytoluene (BHT) is described. The use of BHT in this process suppresses side reactions and enables high-yielding formation of methylene acetals of various diols, including carbohydrate-type substrates.

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Key concepts: Acetal, Chemistry, Methylene, Organic chemistry, Diol, Medicinal chemistry