Water → Benzoic acid, 3-methoxy-4-methyl-, methyl ester

HRID 228888

Reaction equation

HRID 228888 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](O)=[O:6].[C:12](=O)([O-])[O-].[K+].[K+].CI.O.CN(C)[CH:23]=[O:24]>>[CH3:12][O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:24][CH3:23])=[O:6]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 685123-Hydroxy-4-methylbenzoic acid

Product 1

HCID 591123Benzoic acid, 3-methoxy-4-methyl-, methyl esterYield 98%

Procedure

3-Hydroxy-4-methylbenzoic acid (3 g) was dissolved in N,N-dimethylformamide (60 ml) to prepare a solution. Potassium carbonate (6.81 g) and methyl iodide (6.14 ml) were added to the solution, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give methyl 3-methoxy-4-methylbenzoate (3.48 g, yield 98%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-021733848a75406f9c04a04141783cba
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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