Hydrochloric Acid → 2-Nitroresorcinol ditosylate

Participants

Reaction Steps

To a stirred solution of 2-nitroresorcinol (31.0 g, 0.2 mole) and p-toluenesulfonyl(tosyl) chloride (83.9 g, 0.44 mole) in THF (500 ml) at ≤15° C. was added triethylamine (84 ml, 0.6 mole) at such a rate that the temperature did not exceed 15° C. The mixture was stirred two additional hours at ambient temperature. The reaction was then poured into ice water (5 liters) and hydrochloric acid (100 ml) with stirring. The resulting precipitate was collected, air dried, and recrystallized from acetonitrile (250 ml) to yield 85.6 g (92.3 percent) of a white crystalline product. Thin layer chromatography (TLC) showed the product to be pure.

Provenance & Evidence