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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 14
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Original Articles

O-BENZYLATION OF POLYPHENOLICS. PREPARATION OF 1,2,4-TRIBENZYLOXYBENZENE

Uffe Anthoni Marine Chemistry Section, Department of Chemistry, University of Copenhagen, Universitetsparken 5, Copenhagen, DK-2100, Denmark
,
Carsten Christophersen Marine Chemistry Section, Department of Chemistry, University of Copenhagen, Universitetsparken 5, Copenhagen, DK-2100, Denmark
&
Per Halfdan Nielsen Marine Chemistry Section, Department of Chemistry, University of Copenhagen, Universitetsparken 5, Copenhagen, DK-2100, Denmark
Pages 2223-2229 | Received 14 Aug 2000, Published online: 09 Nov 2006
 
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Abstract

The main phenolic by-products in the O-benzylation of 1,2,4-trihydroxy-or 1,2,4-triacetoxybenzene to 1,2,4-tribenzyloxybenzene have been identified as due to incomplete O-benzylation and C-benzylation. In addition, dibenzyldimethylammonium chloride is formed from DMF and benzyl chloride. The main factors controlling these reactions paths are discussed. An efficient procedure for preparing 1,2,4-tribenzyloxybenzene using NaH in DMF is reported.

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