Acetic Acid → 3-Nitro-1-naphthoic acid

Participants

Reaction Steps

To a solution of 3-nitro-1,8-naphthalic anhydride (21.8 g, 89.7 mmol) in H2O (550 mL) containing 14.4 g of NaOH was added a solution of yellow HgO (25.1 g) in a mixture of H2O (75 mL) and glacial AcOH (25 mL). After reflux for 4 days, the reaction mixture was cooled and filtered to afford the mercurated product, which was then refluxed in 700 mL of 5N HCl for 3 h. The cream-colored precipitate was filtered, washed with cold H2O, dried, and recrystallized from hot glacial AcOH to yield 3-nitronaphthalene-1-carboxylic acid (12 g). 1H NMR (300 MHz, DMSO-d6): δ 13.7 (brs, 1H), 9.18 (s, 1H), 8.93 (d, J=8.4 Hz, 1H), 8.70 (s, 1H), 7.88 (t, J=7.8 Hz, 1H), 7.76 (t, J=6.9 Hz, 1H).

Provenance & Evidence