Methanol → Methyl 2-(benzyloxy)acetate

HRID 2169120Notes

Reaction equation

HRID 2169120 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH3:17]O>>[CH3:17][O:11][C:10](=[O:12])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 290301(Benzyloxy)acetic acid

Product 1

HCID 11745225Methyl 2-(benzyloxy)acetate

Conditions

Temperature
0 °C

Procedure

To a stirred solution of benzyloxy-acetic acid (5 g, 30.12 mmol) in methanol (100 mL) was added SOCl2 (2.66 mL, 35.8 mmol) at 0° C. The mixture was stirred for 30 min at 0° C., finally at room temperature for 2.5 h. After completion of the reaction, the solvent was evaporated and the reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution. The separated organic part was dried over sodium sulfate and concentrated under reduced pressure to get benzyloxy-acetic acid methyl ester (3) as a crude colorless oil (4.98 g).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. additionthe reaction mixture was diluted with ethyl acetate
  4. washwashed with saturated aqueous sodium bicarbonate solution
  5. dry with materialThe separated organic part was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfd584c2b2b4476781d71d080118eb18
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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