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Synthesis 2009(6): 929-934  
DOI: 10.1055/s-0028-1087986
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

2-Iodoxybenzoic Acid/Tetraethylammonium Bromide/Water: An Efficient Combination for Oxidative Cleavage of Acetals

Chutima Kuhakarn*a, Waraporn Panchana, Supanimit Chiampanichayakula, Natthapol Samakkanada, Manat Pohmakotra, Vichai Reutrakula, Thaworn Jaipetchb
a Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand
Fax: +66(2)3547151; e-Mail: scckk@mahidol.ac.th;
b Mahidol University, Kanchanaburi Campus, Saiyok, Kanchanaburi 71150, Thailand
Further Information

Publication History

Received 27 June 2008
Publication Date:
02 March 2009 (online)

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Abstract

A simple and efficient procedure has been developed for the oxidation of cyclic and acyclic acetals to the corresponding hydroxyalkyl carboxylic esters and simple esters, respectively. 2-Iodoxybenzoic acid (IBX) in the presence of tetraethylammonium bromide was employed for the reaction in aqueous media. The salient features of the protocol include short reaction time, environmentally benign reagents and solvent, and moderate to high yields.

Key words

o-iodoxybenzoic acid - acetals - oxidations - hydroxyalkyl esters - alcohols

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