Benzyl Alcohol → Benzyl 2-hydroxyacetate

Participants

Reaction Conditions

Reaction Steps

Into a solution of glycolic acid (35 gm, 46 mmol) in benzyl alcohol (200 mL) was bubbled anhydrous hydrogen chloride for 1 hr at 0° C. The reaction was then stirred for an additional 4 hrs at 0° C. before it was poured into a mixture of ice water and ether. The layers were separated and the aqueous layer was reextracted with ether. The ether layers were sequentially washed with sodium bicarbonate and brine, combined, dried over sodium sulfate and evaporated. Distillation of the residue at 103°-110° C. 0.5 mm afforded 59 gm (77%) of benzyl glycolate as a clear liquid.

Provenance & Evidence