Glycolic Acid → Benzyl 2-hydroxyacetate

HRID 1776513Notes

Reaction equation

HRID 1776513 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]([OH:7])=[O:6].[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[OH:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

5

Reactant 3

HCID 757Glycolic AcidHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 561337Benzyl 2-hydroxyacetateYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

NaH (6.31 g, 158 mmol) was suspended in dry THF (500 ml) and cooled to 0° C. 2-hydroxyacetic acid (12 g, 158 mmol) was added portion wise, and the mixture was stirred at RT for 1 hour. The solvent was removed, and the residue was suspended in DMF (500 ml); KI (2.488 g, 14.99 mmol) and benzyl bromide (18.77 ml, 158 mmol) were added; and the mixture was heated to 100° C. for 24 hours. The solvent was removed, and the crude was portioned between EtOAc (600 ml) and water (200 ml). The organic phase was washed with brine and dried over Na2SO4. The solvent was removed and the crude was purified by flash chromatography on silica gel (petroleum ether/EtOAc 80/20). Benzyl 2-hydroxyacetate was obtained (18.089 g, 69% yield).

Workup

  1. customThe solvent was removed
  2. temperatureand the mixture was heated to 100° C. for 24 hours
  3. customThe solvent was removed
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed
  7. customthe crude was purified by flash chromatography on silica gel (petroleum ether/EtOAc 80/20)

Sources & evidence

ORD record
ord-29a2a8304905472d97ef4be8b32a94a1
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

Loading…