Hydrochloric Acid → 3-Formyl-4-methoxybenzamide

Participants

Reaction Steps

3-Dimethoxymethyl-4-methoxybenzoic acid (1.81 g) obtained in step B, 0.65 g of ammonium chloride, 1.48 g of benzotriazol-1-ol monohydrate, and 1.85 g of (3-dimethylaminopropyl)ethylcarbodiimide hydrochloride were dissolved in 50 mL of N,N-dimethylformamide, and 4.20 mL of N,N-diisopropylethylamine was added to the solution. The resulting solution was stirred for 13 hours at room temperature, and then 1M hydrochloric acid was added little by little until the mixture reached nearly pH 2. This mixture was extracted with ethyl acetate twice, whereafter the organic layer combined was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The residue was washed with ethanol, and then dried under reduced pressure to obtain 1.03 g (71%) of 3-formyl-4-methoxybenzamide.

Provenance & Evidence