Nitric Acid → Naphthalic anhydride, 3-nitro-

Participants

Reaction Steps

To a solution of 1,8-naphthalic anhydride (25 g, 0.13 mol) in conc. H2SO4 (100 mL) was added dropwise a solution of conc. HNO3 (7.85 g, 0.13 mol) in conc. H2SO4 (25 mL) at 0° C. After the addition was complete, the resulting mixture was allowed to warm to RT, stirred for 90 min and then poured into ice-H2O. The solid was filtered by suction, washed with H2O, and re-crystallized from glacial AcOH to yield 3-nitro-1,8-naphthalic anhydride (24.5 g). 1H NMR (300 MHz, CDCl3): δ 9.11 (s, 1H), 9.06 (s, 1H), 8.58 (d, J=7.5 Hz, 1H), 8.43 (d, J=7.8 Hz, 1H), 7.82 (t, J=7.8 Hz, 1H).

Provenance & Evidence