Aryl ethyl ethers prepared by ethylation using diethyl carbonate

Abstract

An environmentally more convenient reaction for the production of industrially important aryl ethyl ethers (ArOEts) is described. ArOEts were selectively obtained in essentially quantitative yields by the reaction of corresponding (hetero)aromatic alcohols (ArOHs) with diethyl carbonate as the environmentally friendly alkylating reagent in the presence of N,N-dimethylacetamide used as polar aprotic cosolvent, and sodium ethoxide as the base. The reactions were carried out in the air under atmospheric pressure at 137°C. Reaction equilibrium was shifted by distilling the ethanol from the reaction mixture. All ArOEts were isolated by evaporation of the reaction mixture, and subsequent extraction with water and diethoxymethane. The ethylation agent and used solvents were non-toxic, recyclable and biologically degradable. Wastewater from the extraction was successfully treated by Fenton oxidation and returned to the next work-up process.