Reaction of alkylcarbonyloxymethyl halides with phenols: reevaluating the influence of steric hindrance

Evidence is presented that contradicts an earlier finding that, in the absence of steric hindrance, the coupling reaction of alkylcarbonyloxymethyl (ACOM) halides with phenols favors acylated product. A one-step synthesis is used to generate sterically unhindered ACOM iodides, which are then reacted with several phenols to give mainly alkylated phenol.