Hydrochloric Acid → 2-Chloro-1-(2,5-dimethoxyphenyl)ethanone

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Reaction Steps

In a three-neck round bottom 2 liter flask, 60.0 g (0.434 mol) of 1,4-dimethoxybenzene is added. To the flask is added 300 mL dry dichloromethane to dissolve the solid. When the solution is clear, 63.7 g (0.477 mol) of anhydrous AlCl3 is added through a powder funnel and the funnel is washed with dichloromethane. The resulting solution is yellowish in color. This solution is stirred at room temperature for 5 minutes and 40.0 mL (0.50 mol) chloroacetylchloride in 5 mL dichloromethane is added dropwise (total addition time 1 hour 30 minutes) and is stirred vigorously at room temperature. The color of the solution became is orange-red and then like red wine. The solution is stirred for 4 hours after addition at room temperature and then poured in to a mixture of crushed ice and 126 mL conc. HCl and stirred for 20 minutes again. The organic phase is separated and the aqueous phase is extracted with CH2Cl2 (100 mL×3). Total dichloromethane fractions are combined and washed with H2O (100 mL×2), cold 10% aq. NaOH (200 mL×1) and H2O (100 mL×2) and dried over anhydrous sodium sulfate. The organic phase is evaporated under reduced pressure and the thick solution is cooled to room temperature yielding a yellow solid (59.0 g, yield 64%). The crude product is crystallized from methanol (m.p. 89-91° C.).

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