Nitric Acid → 1-(1-Methylcyclobutyl)-4-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

70% Nitric acid (7:3, Nitric acid:Water, 0.375 ml, 5.92 mmol) was added dropwise over 60 minutes to a solution of (1-methylcyclobutyl)benzene (346 mg. 2.37 mmol) in Acetic anhydride (1.4 mL, 15 mmol) cooled at 0° C. The temperature of the solution was maintained below 5° C. during the addition. Upon completion of the addition, the reaction was stirred for 60 minutes with cooling. The reaction mixture was poured into 40 ml ice water and the ice was allowed to melt. The aqueous phase was extracted with three×20 ml portions of Et2O and the combined organic phase was washed with 25 ml H2O followed by two 20 ml portions of sat NaHCO3 solution. The organic phase was dried over Na2SO4, filtered and concentrated to yield a light the product as an oil (418 mg) which was used as is in the next step. 1H NMR (400 MHz, CDCl3) d ppm 8.16 (d. J=8.71 Hz, 2H), 7.29 (d, J=8.71 Hz, 2H), 2.41 {m, 2H), 2.15 (m, 3H), 1.88 (m, 1H). 1.48 (s, 3H)

Provenance & Evidence