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)

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.

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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.