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Synlett 2010(8): 1190-1192  
DOI: 10.1055/s-0029-1219793
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Oxidative Preparation of Aromatic Orthocarboxylates from Aldehydes

Hiroyuki Tanabeb, Xinyao Hea, Prasath Kothandaramana, Motoki Yamane*a
a Division of Chemistry and Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore
Fax: +6567911961; e-Mail: yamane@ntu.edu.sg;
b Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
Further Information

Publication History

Received 1 February 2010
Publication Date:
31 March 2010 (online)

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Abstract

Aromatic orthocarboxylates are oxidatively synthesized in good yields from hydroxyacetals derived from the corresponding aromatic aldehydes. In situ generation of hydroxyacetal and successive oxidation by DDQ provides a one-pot preparation of aromatic orthocarboxylates from aldehydes.

Key words

orthoester - oxidation - acetal - aldehyde - one-pot reaction

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11

We separated the diastereomers for the purpose of structural analysis of the major stereoisomers. This separation is surely unnecessary for the subsequent step.