Ethylene Glycol → 2-Hydroxyethyl phenoxyacetate

Participants

Reaction Steps

A 2-liter, 3-neck, round-bottom flask was equipped with a heating jacket, thermocouple and Dean-Stark apparatus for water removal. The flask was charged with 152 g (1.0 mole) phenoxyacetic acid, 62 g (1.0 mole) ethylene glycol, 22 g p-toluenesulfonic acid, 260 ml mixed xylenes and swept with nitrogen and sealed under a nitrogen balloon. The flask contents were heated to a pot temperature of 150° C. for 1/2 hour wherein 23 ml of water were collected and the reaction system cooled. Volatiles were removed at 110° C. in 4 mm of Hg vacuum to give a waxy white solid, IR shows formation of ester and disappearance of acid carbonyl, and mass spectrometry shows the molecular weight of 196.

Provenance & Evidence