Methanol → Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

HRID 1739462Notes

Reaction equation

HRID 1739462 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12]O>>[OH:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

3

Reactant 2

HCID 887MethanolHCID 57882-Hydroxy-p-toluic acid

Product 1

HCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl esterYield 90%

Procedure

A solution of 2-hydroxy-4-methylbenzoic acid (20.0 g, 0.132 mol) in methanol (200 ml) was cooled in an ice bath. Concentrated, H2SO4 (20 ml) was added cautiously and the reaction heated to reflux and held at reflux for 48 hours. The reaction was allowed to cool to ambient temperature, the solvent evaporated and the residue purified by chromatography (eluant: CH2Cl2) to give methyl 2-hydroxy-4-methylbenzoate (19.76 g, 90%).

Workup

  1. concentrationConcentrated
  2. additionH2SO4 (20 ml) was added cautiously
  3. temperaturethe reaction heated
  4. temperatureto reflux
  5. temperatureat reflux for 48 hours
  6. customthe solvent evaporated
  7. customthe residue purified by chromatography (eluant: CH2Cl2)

Sources & evidence

ORD record
ord-35bdb43e51b24479b071007d52a5b0fb
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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