Hydrochloric Acid → Benzenemethanol, 4-chloro-alpha-methyl-

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Reaction Steps

4-Chloroacetophenone (15.5 g, 100 mmoles) was dissolved in 100 ml of methanol, and a solution of 5.67 g (150 mmoles) of sodium borohydride in 250 ml of methanol was slowly added to the solution. The resulting solution was stirred overnight at room temperature. To the reaction mixture was added 1 N hydrochloric acid, and the organic layer was extracted with diethyl ether. The organic layer was collected and dried over anhydrous sodium sulfate, followed by concentration to obtain 1-(4-chlorophenyl)ethanol [1H-NMR (300 MHz, CDCl3) 1.48 (d, J=6.3 Hz, 3H), 4.88 (q, J=6.6 Hz, 1H), 7.31 (s, 4H)] in a nearly pure form.

Provenance & Evidence