Nitric Acid → 4,4-Dimethyl-7-nitro-3,4-dihydronaphthalen-1(2H)-one

Participants

Reaction Steps

To 1.7 mL (3.0 g, 30.6 mmol, 18M) H2SO4 at −5iC (ice-NaCl bath) was slowly added 783.0 mg (4.49 mmol) of 3,4-dihydro-4,4-dimethyl-naphthalen-1(2H)-one. A solution of HNO3 (426.7 mg 6.88 mmol, 0.43 ml 16M, and 1.31 g (0.013 mol, 0.74 mL, 18 M of H2SO4 were slowly added. After 20 min, ice was added and the resulting mixture was extracted with EtOAc. The combined extracts were concentrated under reduced pressure to give a yellow oil from which the title compound, a pale yellow solid, was isolated by column chromatography (10% EtOAC/hexanes).

Provenance & Evidence