Methanol → Methyl 2-(3-methoxyphenyl)acetate

HRID 1631943Notes

Reaction equation

HRID 1631943 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.S(=O)(=O)(O)O.[CH3:18]O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH3:18])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 15719(3-Methoxyphenyl)acetic acid

Product 1

HCID 519609Methyl 2-(3-methoxyphenyl)acetate

Procedure

A solution of 25.0 g (150 ml) of (3-methoxyphenyl)acetic acid in dry methanol (250 ml) was mixed with 2 ml of conc. sulfuric acid and heated under reflux for 16 h. The cooled reaction solution was concentrated in vacuo, added to ice-water and extracted four times with 70 ml of ethyl acetate each time. The combined organic extracts were washed with saturated NaCl solution and dried over magnesium sulfate, and the solvent was removed in vacuo. Yield: 28.3 g (100%) of colorless oil

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 h
  3. customThe cooled reaction solution
  4. concentrationwas concentrated in vacuo
  5. additionadded to ice-water
  6. extractionextracted four times with 70 ml of ethyl acetate each time
  7. washThe combined organic extracts were washed with saturated NaCl solution
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cc47b492f71345f7ab927f4cdcb237c2
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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