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Synthesis 2009(8): 1318-1322  
DOI: 10.1055/s-0028-1088025
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Convenient Method for Converting Hydroxyacetophenones into Their Ethylene or Trimethylene Acetals

Fumiaki Ono, Hirotaka Takenaka, Toshikazu Fujikawa, Masaki Mori, Tsuneo Sato*
Department of Life Science, Kurashiki University of Science and the Arts, Kurashiki 712-8505, Japan
Fax: +81(86)4401062; e-Mail: sato@chem.kusa.ac.jp;
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Publication History

Received 6 November 2008
Publication Date:
25 March 2009 (online)

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Abstract

Various types of hydroxyacetophenones are efficiently converted into the corresponding ethylene acetals in the presence of ethane-1,2-diol, triisopropyl orthoformate, and a catalytic amount of cerium(III) trifluoromethanesulfonate under mild reaction conditions. The homologous trimethylene acetals can be also prepared in the same way.

Key words

acetal - cerium(III) trifluoromethanesulfonate - hydroxyacetophenone - Lewis acid - protecting group

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8

No reaction took place when the reaction was carried out in the absence of ethane-1,2-diol.

9

Cyclic acetalization of normal ketones such as octan-2-one and acetophenone proceeded smoothly under similar reaction conditions.