Hydrochloric Acid → 2-Chloro-1-phenylethanol, (+)-

Participants

Reaction Steps

To a slurry solution of 143 mg (0.5 mmol) of (R)-1,1′-bi-2-naphthol in 10 ml of toluene was added 0.5 ml (0.5 mmol) of toluene solution of diisobutylaluminum hydride (1.0 M) at room temperature, and the mixture was stirred at room temperature for 1 hour. Thereto 1.52 ml (20 mmol) of 2-propanol was added and the mixture was stirred further at room temperature for 30 minutes. Thereto 1.55 g (10 mmol) of phenacyl chloride was added and the mixture was stirred at 50° C. for 4 hours. To the mixture were added 6 ml of 1N hydrochloric acid and 20 ml of water to conduct hydrolysis. The mixture was extracted with ethyl acetate and concentrated to obtain an oily product. The after-treatment and the analysis of the product were then carried out in the same manner as described in Example 2.

Provenance & Evidence