Dimethylformamide → Methyl 3-formyl-4-methoxybenzoate

Participants

Reaction Steps

24.8 mL (398 mmol) of methyl iodide were added dropwise to a room temperature suspension of 30.0 g (181 mmol) of 3-formyl-4-hydroxybenzoic acid (from Example 36) and 75 g (542 mmol) of K2CO3 in 250 mL of dry dimethylformamide (DMF). After stirring 4 hours at room temperature, the reaction mixture was diluted with 2 L H2O and extracted four times with 750 mL ethyl acetate. The ethyl acetate extracts were washed three times with 500 mL H2O, one time with 300 mL 1N NaOH, one time with 500 mL H2O, one time with 250 mL brine, and dried over Na2SO4. Filtration, concentration of filtrate and drying under vacuum gave 20.35 g of pure product as pale yellow needles. 58% yield.

Provenance & Evidence