1,3-Cyclohexadiene → HCID 14267379, compound

Participants

Reaction Steps

To a solution of (Z)-cyclohept-2-enone (1.4 g, 10 mmol) in dry toluene was added aluminum chloride (0.67 g, 5 mmol) and the resulting mixture was stirred at room temperature for 40 minutes. A solution of cyclohexadiene (9.62 g, 120 mmol) in toluene was added dropwise, and the mixture was stirred overnight at 40° C. The reaction mixture was filtered through diatomaceous earth and then partition in ethyl acetate/water. The organic layer was washed with sodium bicarbonate solution, dried (magnesium sulfate), filtered, evaporated under vacuum and purified by chromatography on silica gel eluting with 5-10% ether/hexane to provide the title compound: MS (DCl/NH3) m/z 191 (M+H)+, 208 (M+NH4)+.

Provenance & Evidence