Benzyl Alcohol → Benzyl 2-hydroxyacetate

HRID 2226439Notes

Reaction equation

HRID 2226439 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][OH:3].Cl.CCOCC.[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:1]([O:5][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:4])[CH2:2][OH:3]

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 757Glycolic AcidHCID 3283Diethyl Ether

Product 1

HCID 561337Benzyl 2-hydroxyacetateYield 77%

Conditions

Temperature
0 °C

Procedure

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.

Workup

  1. customThe layers were separated
  2. washThe ether layers were sequentially washed with sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. distillationDistillation of the residue at 103°-110° C

Sources & evidence

ORD record
ord-f5177c5832df49978db86cce7c517007
Source dataset
uspto-grants-1994_09
Patent number
US05348953

Reaction notes

Loading…