1-chloro-1-ethynylcyclohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution, cooled to 10° C., of 18.2 mmol (2.5 g) of p-phenetidine in a mixture of ether:water (4:1; 30 ml) containing 24.5 mmol (3.42 ml) of triethylamine there are added, in succession, 0.25 mmol (0.025 g) of CuCl, 0.39 mmol (0.025 g) of Cu and, dropwise, 28.0 mmol (4.0 g) of 1-ethynyl-1-chlorocyclohexane prepared according to the method described in J. Am. Chem. Soc., 83, 725, 1961, starting from 1-ethynylcyclohexanol. After stirring for 4 hours (allowing the temperature to increase towards ambient temperature) the reaction mixture is diluted with ether and then washed with 1N sulphuric acid solution. The ethereal phase is removed and the aqueous phase is neutralised (at 0° C.) using potassium hydroxide pellets and then re-extracted with ether. The organic phase is dried and then concentrated to yield the expected product. washed with 1N sulphuric acid solution The ethereal phase is removed (at 0° C.) re-extracted with ether The organic phase is dried concentrated