Nitric Acid → Methyl 3-(4-nitrophenyl)cyclopentanecarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 65% nitric acid (0.95 mL) and 95% sulphuric acid (1.2 mL) in carbon tetrachloride (2.5 mL) was added dropwise to a solution of methyl 3-phenylcyclopentanecarboxylate (Journal of Organic Chemistry, 1988, 53(17), 4021) (1 g, 4.9 mmol) and the mixture was stirred at 5-10° C. for 2 h. Ice/water (30 mL) was added and the mixture was extracted with DCM (2×50 mL). The extracts were combined, washed with water and dried. The residue was adsorbed onto silica and purified by chromatography eluting with 0-30% EtOAc in hexane to give the title compound (782 mg, 64%) as an oil; 1H NMR δ3.90 (3H, s), 7.94-7.97 (2H, m), 8.03-8.06 (2H, m), 8.09-8.12 (2H, m), 8.33-8.36 (2H, m).

Provenance & Evidence