Methyl iodide → Methyl 2-methoxy-4-methylbenzoate

HRID 1627757Notes

Reaction equation

HRID 1627757 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:13][O:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

Product 1

HCID 7172021Methyl 2-methoxy-4-methylbenzoateYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-hydroxy-4-methylbenzoate (3 g; 18.2 mmol) in DMF (36 mL) was added potassium carbonate (5 g; 36.4 mmol) and methyl iodide (3.35 mL; 182 mmol) dropwise. The reaction mixture was stirred at room temperature for 24 hours. The insoluble's were filtered, washed with ethyl acetate and the volatiles were removed under reduced pressure. The crude material was purified by flash chromatography on silica gel using a gradient of ethyl acetate (1 to 30%) in heptane to furnish 2.78 g of the methyl 2-methoxy-4-methylbenzoate (85%) as a colorless oil.

Workup

  1. filtrationThe insoluble's were filtered
  2. washwashed with ethyl acetate
  3. customthe volatiles were removed under reduced pressure
  4. customThe crude material was purified by flash chromatography on silica gel using a gradient of ethyl acetate (1 to 30%) in heptane

Sources & evidence

ORD record
ord-763172d02ff54bf0a80a37a341ea6a4f
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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