Nitric Acid → 2-Acetamido-5-nitroresorcinol ditosylate

Participants

Reaction Steps

A solution of 2-acetamidoresorcinol ditosylate (11.9 g, 0.025 mole) in acetic anhydride (75 ml) was cooled to below 15° C. Meanwhile, nitric acid (1.9 ml, 0.029 mole) was slowly added to cold acetic anhydride (20 ml) with stirring so that the temperature did not exceed 25° C. The nitric acid solution was then added to the cold acetanalide solution. Finally, the sulfuric acid (0.75 ml) was added. The mixture was stirred an additional six hours, during which time the reaction temperature rose to 30° C. The mixture was pured into ice water (1500 ml) and stirred one hour. The resulting precipitate was collected, air dried, and recrystalllized from isopropyl alcohol (100 ml) to yield a tan crystallline solid (9.9 g, 76.0 percent). TLC showed the product to be pure.

Provenance & Evidence