2-Chlorobenzyl chloride → 1-Chloro-2-(4-chlorophenyl)-3-(2-chlorophenyl)propan-2-ol

Participants

Reaction Conditions

Reaction Steps

5.0 g (0.031 mol) of 2-chlorobenzyl chloride are added within 5 minutes at from 24° to 36° C. to 9.7 g (0.404 mol) of magnesium turnings in 20 ml of absolute ether. After the reaction has commenced, a solution of 200 ml of absolute ether and 50.2 g (0.31 mol) of 2-chlorobenzyl chloride is added dropwise. The mixture is subsequently refluxed for about a further 10 minutes, the excess magnesium is decanted off under nitrogen, and the Grignard solution is cooled to 0° C. 55.7 g (0.3 mol) of para-chloro-ω-chloroacetophenone dissolved in 350 ml of toluene are then added dropwise, and the reaction mixture is stirred at 0° C. for 1.5 hours and added dropwise at from about 2° to 6° C. to 1.5 l of concentrated ammonium chloride solution. Extraction with methyl tert.-butyl ether and subsequent conventional work-up gives 92.9 g (yield 99%, purity according to HPLC: 68.2%) of 1-chloro-2-(4-chlorophenyl)-3-(2-chlorophenyl)propan-2-ol as a crude oil, which can be further reacted directly. For characterization, the product was recrystallized from n-hexane.

Provenance & Evidence