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Synlett 1997; 1997(8): 921-922
DOI: 10.1055/s-1997-939
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Chloromethyl(dimethyl)sulfonium Trifluoromethanesulfonate - The Reagent for Preparation of Acetals of 2-Hydroxyaldehydes from Ketones under Basic Conditions

Grzegorz Kaczmarczyk, Andrzej Jończyk*
  • *Warsaw University of Technology, Faculty of Chemistry, Koszykowa 75, 00-662 Warszawa, Poland, Fax 0048-22-6282741, e-mail: anjon@ch.pw.edu.pl
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Publication Date:
31 December 2000 (online)

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2-Hydroxyaldehydes dimethylacetals 5 are synthesized via reaction of chloromethyl(dimethyl)sulfonium trifluoromethanesulfonate (1) with ketones 2, carried out in the presence of sodium methoxide in methanol. The corresponding 2-chloro- (3a) or 2-dimethylsulfonium-oxirane (3b) are presumably transient intermediates.

α-chlorosulfonium salt - sulfonium (dimethyl)chloromethylide - acetals of 2-hydroxyaldehydes