Methyl iodide → Methyl 2-methoxy-4-methylbenzoate

HRID 1688315Notes

Reaction equation

HRID 1688315 reaction equation
C[C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].CI.[C:16](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:13][O:12][C:3]1[CH:2]=[C:10]([CH3:11])[CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH3:16])=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18993555HCID 18993555, compound

Product 1

HCID 7172021Methyl 2-methoxy-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2-methoxy-4-methylbenzoic acid (1.5 g, 9.0 mmol, 1 eq) was dissolved in DMF, methyl iodide (0.86 ml, 13.5 mmol, 1.5 eq) was added to it followed by the addition of potassium carbonate (3.11 g, 22.5 mmol, 2.5 eq). The above mixture was stirred at room temperature for 12 h. Finally, the reaction mixture was passed through celite. The filtrate was evaporated and water was added and the product was extracted with ethyl acetate. The organic layer was washed with water and concentrated. Yield: 1.6 g (98%). 1H NMR (400 MHz, CDCl3): δ 2.31 (s, 3H), 3.86 (s, 3H), 3.89 (s, 3H), 6.77 (s, 1H), 6.79 (d, 1H), 7.14 (d, 1H).

Workup

  1. customThe filtrate was evaporated
  2. additionwater was added
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-65b61329bd59479cab15e64d4b60c5f7
Source dataset
uspto-grants-2012_04
Patent number
US08148382B2

Reaction notes

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