Acetic Acid → 2-Cyclohexyl-5-ethylpyridine

Participants

Reaction Steps

8.71 g (87 mmol) of 2-ethylmalonaldehyde, 16.8 g (79 mmol) of 1,3-diphenylurea, 10.0 g (79 mmol) of methyl cyclohexyl ketone, 11.9 ml (198 mmol) of acetic acid and 39 g (500 mmol) of ammonium acetate were dissolved in 160 ml of 2-propanol, and 5.3 g (39.5 mmol) of chlorosulfonic acid was added dropwise thereto at room temperature. The reaction solution was allowed to undergo the reaction at 80° C. for 2 hours. After completion of the reaction, this was cooled to room temperature, neutralized with 200 g (1.2 mol) of 25% sodium hydroxide aqueous solution and then extracted three times with 200 ml of toluene. The organic layer was concentrated and then purified by distillation under a reduced pressure to obtain 10.8 g (yield 72%) of the title compound (purity 99.3%, melting point 79-81° C.).

Provenance & Evidence