Dimethylformamide → Methyl 3-acetyl-4-methoxybenzoate

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1O)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].CI.[C:16](=O)([O-])[O-].[K+].[K+].CN([CH:25]=[O:26])C>>[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:26][CH3:25])[C:7]([O:9][CH3:16])=[O:8])(=[O:3])[CH3:2]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 91792453-Acetyl-4-hydroxybenzoic acid

Product 1

HCID 10798398Methyl 3-acetyl-4-methoxybenzoate

Procedure

3-Acetyl-4-hydroxybenzoic acid (3.60 g, 20 mmol) and methyl iodide (5.68 g, 40 mmol) were dissolved in 60 ml of DMF, followed by the addition of 11.06 g (80 mmol) of potassium carbonate. The resulting mixture was stirred at room temperature for 2 hours. The DMF was distilled off under reduced pressure, followed by the addition of water. The resulting mixture was extracted with chloroform. The organic layer was dried over MgSO4, the solvent was distilled off under reduced pressure, and the residue was recrystallized from acetone-hexane, whereby 1.42 g of the title compound were obtained as brown powder (yield: 34%).