2-Hydroxy-p-toluic acid → Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

HRID 1642646Notes

Reaction equation

HRID 1642646 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][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO>[CH3:12][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:2]=1[OH:1]

Participants

5

Reactant 2

HCID 57882-Hydroxy-p-toluic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-hydroxy-4-methylbenzoic acid (1.52 g, 10 mmol) in toluene (6 mL) and methanol (2 mL) at 0° C. is added trimethylsilyldiazomethane (2 M in hexane, 6 mL, 12 mmol) dropwise. The mixture is then warmed up to ambient temperature and it is stirred for 2 h. The solvent is removed under reduced pressure and the residue is purified by flash chromatography to give the title compound as a colorless oil.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-78ab623274144e5d82e57e43937ed021
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

Loading…