Glycolic Acid → Benzyl 2-hydroxyacetate

HRID 2041860Notes

Reaction equation

HRID 2041860 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].C(N(CC)CC)C.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)(=O)C>CC(C)=O.ClCCl>[C:1]([O:5][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:4])[CH2:2][OH:3]

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 8857Ethyl Acetate

Product 1

HCID 561337Benzyl 2-hydroxyacetateYield 51.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  1. filtrationThe solution was filtered
  2. customto remove
  3. customprecipitated triethylammonium bromide
  4. concentrationwas concentrated en vacuo
  5. customPurification
  6. customto remove the non-polar impurities

Sources & evidence

ORD record
ord-915753f9f1aa4251b07fea1547729bd5
Source dataset
uspto-grants-2013_11
Patent number
US08586369B2

Reaction notes

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