Hydrochloric Acid → 2-Oxocyclohexanecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

To ethyl 2-oxocyclohexanecarboxylate (2.0 g, 0.01 mmol), 5N NaOH (0.56 g, 0.014 mmol) dissolved in water (3.0 mL) was added at room temperature and stirred for 16 h. The reaction mixture was cooled to 0° C., conc. HCl (1.2 mL) was added and stirred for 45 min. to give 2-oxocyclohexanecarboxylic acid. In another setup, 2,3-dichloroaniline (1.8 g, 11.0 mmol), dissolved in H2O (10 mL) was cooled to 0° C., conc. HCl (6 mL) was added slowly and stirred for 20 min. NaNO2 (0.77 g, 11.0 mmol) in water (5.0 mL) was added and stirred at 0° C. for 30 min., filtered, the filtrate was cooled to 0° C. and 2-oxocyclohexanecarboxylic acid (prepared above) (1.6 g, 11.6 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred for 30 min. during which time a yellow solid was precipitated. The solid was filtered and air dried to give the title compound as a yellow solid (1.7 g, 56%). 1H NMR (200 MHz, CDCl3, δ in ppm) 13.87 (bs, 1H), 7.65 (dd, J=8.4, 1.8 Hz, 1H), 7.26-7.04 (m, 2H), 2.77-2.71 (m, 2H), 2.61-2.54 (m, 2H), 1.91-1.85 (m, 4H).

Provenance & Evidence