Nitric Acid → 5-Nitronaphthalene-2,3-diol

Participants

Reaction Conditions

Reaction Steps

A suspension of 5.0 g of 2,3-Dihydroxynaphthalene dimesitylate in 50 ml of acetic anhydride was treated with 12 ml of 70% HNO3 at such a rate as to keep the temperature between 37-40° C. A cooling bath should be kept under the flask, ready to be raised if necessary, as the temperature should not be allowed to exceed 45° C. The 12.0 ml of nitric acid was added to the reaction mixture over a period of 1-2 h. After 2 h, the reaction mixture was cooled to 5° C. in an ice bath and the precipitate was collected by filtration and washed with ether. Yield 5-Nitro-2,3-dihydroxynaphthalene dimesitylate 70%; mp 199-201° C., 1H NMR (DMSO-d6) δ 3.58 (s, 6H), 7.76 (t, J=8.0 Hz, 1H), 8.25-8.65 (m, 4H)

Provenance & Evidence