2-Phenylethanol → 2-Chloro-1-[4-(2-hydroxyethyl)phenyl]ethan-1-one

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Reaction Conditions

Reaction Steps

Finely ground AlCl3 (92.0 g, 0.69 mol) was mixed with dichloromethane (120 ml) in a flask and cooled to -10° C. Chloracetyl chloride (37.3 g, 0.33 mol) was added to the mixture as it was kept cool. Phenethyl alcohol (36.6 g, 0.30 mol) was dissolved in dichloromethane (20 ml) and charged to a dropping funnel. The phenethyl alcohol solution was added slowly dropwise to the mixture over 2 hours while stirring and keeping the temperature at about 10° C. At the end of the addition, the mixture was allowed to warm to room temperature and stirred overnight. The red color solution was poured into a large quantity of ice (about 300 g). The organic layer was separated and the aqueous layer was extracted with dichloromethane (200 ml), and the dichloromethane portions were washed with water until neutral. The organic phase was then dried (magnesium sulfate), concentrated, recrystallized (ether), and dried to give 48.8 g (81.9%) of compound 5. Analysis of the products gave the following results: mp 41°-45° C.; NIR (KBr) 3477, 3355, 2947, 1702, 1693, 1606, 1218, 1044, 818 cm-1 ; 1H NMR (60 MHz) δ 1.96 (s, 1H), 2.92 (t, 2H, J=6.5 Hz), 3.90 (t, 2H, J=6.5 Hz), 4.67 (s,2H), 7.2-7.4 (m, 2H), 7.8-8.0 (m, 2H).

Provenance & Evidence