Steric hindrance is a key factor in the coupling reaction of (acyloxy) alkyl-α-halides with phenols to make a new promoiety for prodrugs

A convenient and mild method for the synthesis of various (acyloxy) alkyl-α-ethers of phenols was described. (Acyloxy) alkyl-α-halides were conjugated with phenols in acetone in the presence of cesium carbonate to give (acyloxy) alkyl-α-ethers of phenols. Steric hindrance is a key factor governing this reaction and greater steric hindrance favors the alkylation product over the acylation product.