Nitric Acid → 7-Nitro-1-tetralone

Participants

Reaction Steps

Under ice-cooling, 1-tetralone (15.0 g, 0.103 mol) was gradually added dropwise to fuming nitric acid (100 ml). The reaction mixture was stirred for 30 minutes, which was poured into water. Resulting crystalline precipitate was collected by filtration and washed with water, which was dissolved in ethyl acetate. The solution was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from ethyl acetate/isopropyl ether to give 7-nitro-1-tetralone. This compound was dissolved in ethanol (100 ml), to which 5% Pd.-C (50% hydrous, 1 g) was added. The mixture was stirred for 2 hours at room temperature under hydrogen atmosphere. The reaction mixture was subjected to filtration, and the filtrate was concentrated. The concentrate was purified by means of a silica gel column chromatography (hexane/ethyl acetate, 3:2), followed by recrystallization from ethyl acetate/isopropyl ether to give 1.70 g (yield from 1-tetralone, 10%) of the above-titled compound, m.p.141-143° C.

Provenance & Evidence