4-Hydroxybenzaldehyde → N-(ethoxycarbonylmethyl)-2-(4-formylphenoxy)acetamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-hydroxybenzaldehyde (6.1 g), potassium carbonate (13.8 g), sodium iodide (0.75 g) and dimethylformamide (110 ml) was added N-(ethoxycarbonylmethyl)-2-chloroacetamide (8.9 g), and the mixture was stirred at 80° C. for 30 minutes. The reaction mixture was poured into 3% hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue was chromatographed on silica gel column (eluent; ethyl acetate), the desired fractions were collected and recrystallized from ethyl acetate/hexane to give N-(ethoxycarbonylmethyl)-2-(4-formylphenoxy)acetamide (4.09 g).

Provenance & Evidence