Acetonitrile → 2-methoxy-1,3-benzenedicarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

2-Hydroxy-1,3-benzenedicarboxaldehyde (1.05 g, 7 mmol), dimethyl sulfate (1.06 g, 8.4 mmol), and 55 mL of acetonitrile were charged into a 1-necked flask equipped with a mechanical stirrer. 1.45 g (10.5 mmol) of potassium carbonate was added at room temperature under nitrogen. The mixture was stirred at 75° C. until GC-MS indicated that the reaction was complete. The reaction mixture was cooled to ambient temperature, diluted with diethyl ether, washed with NaCl/H2O, and dried over MgSO4. The ether was evaporated off. The crude product was recrystallized from diethyl ether. Pale yellow solid (0.62 g, 54% yield) was obtained. 1H NMR in CDCl3 was consistent with the proposed structure. 1H NMR (CDCl3): δ 10.4 (2H), 8.1 (2H), 7.4 (1H), 4.1 (3H).

Provenance & Evidence