O-benzylation of polyphenolics. Preparation of 1,2,4-tribenzyloxybenzene

Authors
Anthoni, U Christophersen, C Nielsen, PH
Citation
U. Anthoni et al., O-benzylation of polyphenolics. Preparation of 1,2,4-tribenzyloxybenzene, SYN COMMUN, 31(14), 2001, pp. 2223-2229
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
31
Issue
14
Year of publication
2001
Pages
2223 - 2229
Database
ISI
SICI code
0039-7911(2001)31:14<2223:OOPPO1>2.0.ZU;2-R
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 a s due to incomplete O-benzylation and C-benzylation. In addition, dibenzyld imethyl-ammonium chloride is formed from DMF and benzyl chloride. The main factors controlling these reactions paths are discussed. An efficient proce dure for preparing 1,2,4-tribenzyloxybenzene using NaH in DMF is reported.