Formaldehyde → N-(hydroxymethyl)benzamide

Participants

Reaction Conditions

Reaction Steps

Benzamide (25 g, 206 mmol), formaldehyde (37% aqueous, 70 mL, 890 mmol), and potassium carbonate (700 mg, 5 mmol) were mixed in 36 mL of water. The mixture was heated at 45° C. long enough to dissolve the reagents and then cooled to room temperature. The reaction was allowed to proceed for 48 hours when 1H NMR indicated that the reaction was complete. The reaction was diluted with about 500 mL of water and crystals began to form and were allowed to continue to form for 18 hours. The crystals were collected by vacuum filtration, washed with water, and vacuum dried at 40° C. The filtrate was extracted with ethyl acetate and the organic layer was dried over sodium sulfate, filtered, and evaporated to give a white solid which was also vacuum dried at 40°C. The lots were combined for a total of 29.0 g of title compound. 93%. 1H NMR consistent with title compound.

Provenance & Evidence