Benzyl Chloride → HCID 13275938, compound

Participants

Reaction Steps

Benzylmagnesium chloride was prepared by reacting benzyl chloride (37.0 ml, 0.320 mol) with magnesium turnings (8.50 g, 0.350 mol) in 125 ml anhydrous ether (under N2). Then, a solution of 2-adamantanone (24.03 g, 0.160 mol) in 250 ml anhydrous ether was added gradually over a period of 60 minutes. The resulting suspension was stirred at room temperature for 18 hours, and then quenched by cautious addition of 250 ml 2N hydrochloric acid. The organic layer was separated, washed with water, then dried over MgSO4, and the solvent evaporated leaving, after crystallization from pentane, 32.47 g (84%) of 2-(phenylmethyl)-tricyclo[3.3.1.13,7 ]-decan-2-ol. Mp 58°-60° C. The decanol compound was then dehydrated using the method of Keul1 to produce 2-(phenyl-methylene)-tricyclo[3.3.1.13,7 ]decane. The dehydration procedure was as follows:

Provenance & Evidence