Acetone → Methyl 2-methoxy-5-methylbenzoate

HRID 742381

Reaction equation

HRID 742381 reaction equation
[CH3:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].CC(C)=O.S([O:27][CH3:28])(OC)(=O)=O>O>[CH3:12][O:11][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=1[C:7]([O:27][CH3:28])=[O:9]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl Sulfate2×HCID 69735-Methylsalicylic acidHCID 11430Potassium Carbonate

Product 1

HCID 10241396Methyl 2-methoxy-5-methylbenzoateYield 91.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.07 g (33.32×10-3 mol) of 5-methylsalicylic acid and 22.33 g (161.6×10-3 mol) of anhydrous potassium carbonate are introduced into a 250-cm3 two-necked flask. 175 cm3 of anhydrous acetone are added under an inert atmosphere. The reaction mixture is stirred, 7.25 cm3 (76.62×10-3 mol) of dimethyl sulfate are added with a syringe and the mixture is brought to reflux for 6 h. Hydrolysis of the dimethyl sulfate is performed by adding 5 cm3 of water. After filtration and evaporation of the solvent, the residue is taken up with dichloromethane, dried over MgSO4 and then evaporated to dryness. The crude product is purified by chromatography on a silica column (eluent: CH2Cl2) to give 5.47 g (30.36×10-3 mol) of the expected ester, equivalent to a 91% yield.

Workup

  1. temperatureto reflux for 6 h
  2. filtrationAfter filtration and evaporation of the solvent
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customThe crude product is purified by chromatography on a silica column (eluent: CH2Cl2)

Sources & evidence

ORD record
ord-8b4795bf365c43889236d76c78afe510
Source dataset
uspto-grants-1996_09
Patent number
US05554642

Linked notes

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