Acetic Acid → 6-Methoxy-7-nitro-1,2,3,4-tetrahydronaphthalen-1-one

Participants

Reaction Steps

6-Methoxy-1-tetralone (12.0 g, 68.1 mmol) was dissolved in acetic anhydride (60 ml), a fuming nitric acid (4.8 ml)-acetic acid (4.2 ml) mixed solvent was slowly added dropwise under ice-cooling with stirring, and thereafter the mixture was stirred at the same temperature for 2 hr. The reaction mixture was diluted with ether, and the precipitated solid was collected by filtration and dried under reduced pressure. The obtained solid was recrystallized from benzene (100 ml), and the precipitated solid was filtered, dried under reduced pressure to give the title compound (3.62 g, yield 24%) as a colorless solid.

Provenance & Evidence