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

HRID 228888

Reaktionsgleichung

Reaktionsgleichung von HRID 228888
[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]

Komponenten

6

Edukt 5

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

Produkt 1

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

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-021733848a75406f9c04a04141783cba
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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