Catalytic Hydroxyethylation of Phenols with Renewable Ethylene Glycol Diester as an Alternative to Ethylene Oxide

Abstract

Polyol esters are abundant bio‐based resources. Integration of polyol esters into the production chain of fine chemicals would reduce carbon emission and improve the sustainability of the chemical industry. An efficient synthetic route towards phenoxyethanols was developed through catalytic hydroxyethylation of phenols with ethylene glycol diacetate as the reagent. This method showed the potential of ethylene glycol diester as a safe and sustainable substitute for ethylene oxide, a useful but toxic reagent. A variety of phenoxyethanol esters were produced in high yield under simple catalytic conditions. Mechanism studies revealed the reaction underwent a neighboring group participation process.