Simple and rapid p-methoxybenzylation of hydroxy and amide groups at room temperature by NaOt-Bu and DMSO

The p-methoxybenzylation of hydroxy and amide groups by p-methoxybenzyl chloride utilizing NaOt-Bu in DMSO is described. p-Methoxybenzylation of sterically hindered menthol using NaOt-Bu in DMSO proceeded faster than the commonly used methods which use NaH in THF or DMF for p-methoxybenzylation of hydroxy and amide groups. The described method was applicable for sterically hindered substrates at room temperature without adding any activating reagents such as tetrabutylammonium iodide.