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Synlett 2004(9): 1575-1576  
DOI: 10.1055/s-2004-829535
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Aromatic Aldehydes by Oxidative Hydroxymethylation

Olena Branytska, Ronny Neumann*
Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, 76100, Israel
Fax: +972(8)9344142; e-Mail: Ronny.Neumann@weizmann.ac.il;
Further Information

Publication History

Received 1 April 2004
Publication Date:
29 June 2004 (online)

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Abstract

A new high yield method for the synthesis of aromatic ­aldehydes has been developed. The procedure is based on an acid catalyzed hydroxymethylation of an arene substrate by paraformaldehyde with concurrent selective oxidation of the intermediate aromatic carbinol by 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to the aldehyde product.

Key words

aldehydes - arenes - electrophilic aromatic substitutions - oxidations - quinones

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