Ethylene Glycol → 1-[4-(Ethoxycarbonyl)phenyl]ethanone-ethyleneacetal

Participants

Reaction Steps

9.61 g of 4-acetylbenzoic acid ethyl ester (supplied from the firm Wako Pure Chem. Ind.) were dissolved in 200 ml of toluene and thereto were added 20 ml of ethylene glycol and 200 mg of p-toluenesulfonic acid hydrate under argon atmosphere, whereupon the mixture was heated under reflux for 24 hours on Dean-Stark apparatus while removing water. The reaction mixture was then cooled down to room temperature and the toluene layer was washed with water (twice with each 100 ml) and, then, with saturated aqueous sodium chloride solution (100 ml), followed by drying and evaporation to dryness under a reduced pressure, whereby the above-identified compound (12.76 g ) was obtained. Rf=0.58 (ethyl acetate/n-hexane of 1/2).

Provenance & Evidence