In a 3-l. three-necked flask, fitted with a mechanical stirrer, a reflux condenser, and a separatory funnel, are placed 24.3 g. (1 gram atom) of magnesium turnings, 500 cc. of absolute ether, a crystal of iodine, and a 5- to 10-cc. portion of 126.5 g. (115 cc., 1 mole) of freshly distilled benzyl chloride (b.p. 177–179°). In a few minutes the reaction starts (Note 1) and is controlled if necessary by cooling with a wet towel. The stirrer is started, and the balance of the benzyl chloride is run in as fast as the refluxing will permit. The addition requires from one to two hours, and when completed the mixture is refluxed on the steam bath with stirring for three hours. With the stirrer still running, 182 g. (1 mole) of benzophenone (Org. Syn. Coll. Vol. I, 1941, 95) dissolved in 500 cc. of absolute ether is added at such a rate that the mixture refluxes rapidly. This requires about twenty minutes, and then the reaction mixture is allowed to stand for two hours (Note 2).

The flask is placed in an ice bath, 700 g. of cracked ice is added, and the magnesium hydroxide is dissolved by adding 500 cc. of cold 20 per cent sulfuric acid. The ether layer is separated, and the water layer extracted with two 200-cc. portions of ether. The ether is distilled from the combined extracts, and the residual liquid is refluxed for two hours with 100 cc. of 20 per cent sulfuric acid to dehydrate the carbinol. The layers are separated and the product vacuum-distilled (Note 3). The fraction boiling at 215–225°/15 mm. weighs 160–170 g. and melts at 60–68° (Note 4). Crystallization from 900 cc. of hot 95 per cent alcohol and cooling to 0° gives 140–150 g. of the hydrocarbon melting at 68–69° (54–59 per cent of the theoretical amount). Concentration of the mother liquor to 150 cc. and cooling gives 5–10 g., m.p. 65–67.5° (Note 5).