Nitric Acid → HCID 178525695, compound

Participants

Reaction Steps

A mixture of concentrated sulphuric acid (1.5 mL) and concentrated nitric acid (0.9 mL) was added dropwise to a vigorously stirred solution of trans-4-phenylcyclohexanecarboxylic acid (1.7 g. 8.3 mmol) in nitrobenzene (4 mL) at 5° C. The reaction mixture was warmed to room temperature and stirred for 2.5 h and then poured onto ice. The aqueous mixture was extracted with DCM and the organic layer was concentrated in vacuo to leave a yellow oil, which crystallised to a white solid upon standing. The solid was triturated with toluene and filtered to give the title compound (600 mg, 60%) as a solid; 1H NMR δ 1.4-1.6 (4H, m), 1.75-1.9 (2H, m), 1.95-2.1 (2H, m), 2.2-2.38 (1H, m), 2.64-2.77 (1H, m), 7.52 (2H, d), 8.15 (2H, d); MS m/e (M−H)− 248.

Provenance & Evidence