Glycolic Acid → Benzyl 2-hydroxyacetate

Temperature

25 °C

Alternatively, to a cold (0° C.) suspension of NaH (3.8 g of a 60% weight dispersion in mineral oil, 95.0 mmol) in THF (50 mL) was added a solution of glycolic acid (7.2 g, 95 mmol) in THF (50 mL) dropwise via cannula. The resulting solution was warmed to 25° C. and concentrated in vacuo. The resulting salt was suspended in DMF (100 mL) and treated with KI (1.57 g, 0.1 eq) and benzyl bromide (12.3 mL, 1.1 eq). The mixture was heated at 100° C. for 23 hours under argon and the DMF was evaporated. The residue was dissolved in ether and washed with water, saturated Na2S2O3, and brine, and dried over MgSO4. Distillation afforded benzyl glycolate (8.5 g, 54%) as a colorless oil, b.p. 85°-87° C. (0.5 Torr).

1. concentrationconcentrated in vacuo
2. temperatureThe mixture was heated at 100° C. for 23 hours under argon
3. customthe DMF was evaporated
4. dissolutionThe residue was dissolved in ether
5. washwashed with water, saturated Na2S2O3, and brine
6. dry with materialdried over MgSO4
7. distillationDistillation

ORD record

ord-90272677c9df47d4a664ba3ee08ac5ca

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05773428