The benzylation of cresol was studied under liquid-liquid and solid-liquid phase transfer catalytic conditions. Microwave irradiation was useful only in the solid-liquid phase benzylations. Using acetonitrile as the solvent, the benzylations were fully O-selective, but complete conversions were obtained only in the presence of Cs2CO3. There was no need to use an onium salt. In the absence of solvent, an O-selectivity of ca. 90% could be obtained in the presence of an alkali carbonate and an onium salt. The optimum set of conditions was extended to the reaction of other phenol derivatives and alkylating agents.
Keywords: O-alkylation, selectivity, phase transfer catalysis, microwave synthesis
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