Methanol → Methyl 2-(3-methoxyphenyl)acetate

HRID 1643926Notes

Reaction equation

HRID 1643926 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-c1865e376e504f3cba4cc30c612e49de
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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