Methyl iodide → 2-Methylbicyclo(2.2.1)heptan-2-ol

Participants

Reaction Steps

A Grignard reagent was prepared from 96 g (4.0M) of magnesium flakes and 553.0 g (3.9M) of methyl iodide in 600 ml of absolute diethyl ether under a nitrogen gas stream in the conventional manner. 225.0 g (2.05M) of norbornanone (I) (manufactured by Aldrich Chemical Co., Inc.) was added dropwise thereto at room temperature and the resulting mixture was stirred at room temperature over night. The reaction mixture was poured into 800 ml of a saturated aqueous solution of ammonium chloride. The organic phase was collected and dried over anhydrous magnesium sulfate. After evaporation of the ether, the residue was distilled under reduced pressure to give 250.1 g (theoretical yield: 97%) of the aimed compound (II) as a colorless oily material. b.p.: 75° C./18 mmHg.

Provenance & Evidence