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

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, dibenzyldimethyl-ammonium 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.