Glycolic Acid → Benzyl 2-hydroxyacetate

Participants

Reaction Conditions

Reaction Steps

Glycolic acid (200 mg, 2.6 mmol) and triethylamine (401 μL, 2.86 mmol) were dissolved in 2.6 mL of acetone. After a couple minutes of stirring, benzyl bromide (279 μL, 2.34 mmol) was added to the solution. The reaction was refluxed at 60° C. for 12 h. The solution was filtered to remove precipitated triethylammonium bromide and was concentrated en vacuo. Purification was done by silica chromatography with dichloromethane (DCM) to remove the non-polar impurities and then 2% ethyl acetate (EtOAc) in DCM to elute the desired product as a colorless oil (200 mg, 51% yield). 1H-NMR (400 MHz, CDCl3) δ 7.362 (5H, s) δ 5.198 (2H, s) δ 4.201 (2H, s) δ 3.366 (1H, s) ppm.

Provenance & Evidence