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.