A Practical Method for p-Methoxybenzylation of Hydroxy Groups Using 2,4,6-Tris(p-methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM)

Abstract

A new acid-catalyzed p-methoxybenzylating reagent, 2,4,6-tris(p-methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM), has been developed. The reaction of acid- and alkali-labile alcohols with TriBOT-PM in the presence of a catalytic amount of various acids (TfOH, BF₃·OEt₂, CSA, etc.) afforded the corresponding p-methoxybenzyl ethers in good yields. Since TriBOT-PM is an air-stable crystalline solid and can be prepared from inexpensive materials, i.e. cyanuric chloride and anisyl alcohol, this route is of practical use.

Key words

benzylation - protecting groups - cations - ethers - alkylation

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Although TriBOT-PM has been investigated for several applications, it has not been investigated as a p-methoxy-benzylating reagent:
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