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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 and Hiromichi Fujioka*

*Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565-0871, Japan, Email: fujiokaphs.osaka-u.ac.jp

T. Maegawa, Y. Koutani, K. Otake, H. Fujioka, J. Org. Chem., 2013, 78, 3384-3390.

DOI: 10.1021/jo4000256 (free Supporting Information)


Abstract

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

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Key Words

acetals, DBDMH


ID: J42-Y2013-0860