Acetone → Methyl 3-methoxy-5-methylbenzoate

HRID 2390767Notes

Reaction equation

HRID 2390767 reaction equation
[OH:1][C:2]1C=C(C=C(C)C=1)C(O)=O.[C:12](=[O:15])([O-])[O-:13].[K+].[K+].[CH3:18]I.CN([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25]N=1)C.[CH3:29][C:30](C)=O>>[CH3:2][O:1][C:26]1[CH:27]=[C:28]([CH:23]=[C:29]([CH3:30])[CH:25]=1)[C:12]([O:13][CH3:18])=[O:15]

Participants

6

Reactant 5

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 218852-DimethylaminopyridineHCID 2317563-Hydroxy-5-methylbenzoic acid

Product 1

HCID 13834966Methyl 3-methoxy-5-methylbenzoateYield 93.5%

Procedure

To acetone (180 mL) were added 3-hydroxy-5-methylbenzoic acid (9 g, 59.16 mmol), potassium carbonate (33 g, 237 mmol) and methyl iodide (37.2 mL, 591.6 mmol). For O-methylation, the resulting mixture was heated at 65° C. for 12 hours in the presence of a catalytic amount of dimethylaminopyridine. After vacuum distillation of the acetone, the concentrate was treated in water (300 mL) and dichloromethane (450 mL). The organic layer was dried over anhydrous magnesium sulfate and subjected to distillation. Column chromatography (silica gel, ethyl acetate-hexane 1:12 v/v) with the residue produced the title compound as a colorless liquid (9.98 g, 93.5%).

Workup

  1. distillationAfter vacuum distillation of the acetone
  2. additionthe concentrate was treated in water (300 mL)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationsubjected to distillation

Sources & evidence

ORD record
ord-4943c0aa57844adf823ef184858acff4
Source dataset
uspto-grants-2012_09
Patent number
US08273880B2

Reaction notes

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