Nitric Acid → 8-methoxy-5-nitro-3,4-dihydro-1(2H)-naphthalenone

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Reaction Conditions

Reaction Steps

A solution of 8-methoxy-1-tetralone (2.26 g, 13 mmol) (prepared as described in Chatterjee, A. Tetrahedron, (1980), 36, 2513-2520) in acetic anhydride (11.5 mL) was cooled to 0° C., treated with a mixture of fuming nitric acid (0.90 mL) in acetic acid (0.70 mL) dropwise over 1 hour, stirred at 0° C. for 1.5 hours, treated with water (150 mL) and extracted with diethyl ether (300 mL). The diether ether layer was washed with water (150 mL), washed with sodium bicarbonate solution (3×), washed with brine, dried (MgSO4), filtered and concentrated. Purification of the residue on silica gel using a gradient of 2:1 and then 3:2 and finally 1:1 hexanes:ethyl acetate provided the desired product as the more polar isomer.

Provenance & Evidence