Ethylene Glycol → 2-Hydroxyethyl phenoxyacetate

Participants

Reaction Steps

Into a 5000 ml. 3-necked flask, equipped with thermometer, stirrer, condenser and Dean-Stark trap were weighed 924 gms. of phenoxyacetic acid. There were added 2 gms. toluene sulfonic acid as catalyst and 100 mls. of benzene. Heating was started with stirring and there were added 2270 gms. of ethylene glycol. At reflux temperature water was collected and taken off. After 11 and 1/2 hours of refluxing the reaction mixture was transferred to a 6 liter separatory funnel where excess ethylene glycol was separated and recovered. The benzene layer was extracted with hot water and sodium bicarbonate and the benzene layer was filtered warm through a molecular sieve to remove residual water. The benzene extract was allowed to stand overnight and the crystals which formed were removed by filtration and dried in a vacuum oven. A total of 370.2 gms. product was recovered, m.p. 61°-63° C.

Provenance & Evidence