2,2',4'-Trichloroacetophenone

Chemical Properties

Uses

General Description

Air & Water Reactions

Reactivity Profile

Fire Hazard

Synthesis

79-04-9

541-73-1

4252-78-2

To a three-necked flask equipped with a stirrer was added 1,3-dichlorobenzene (147 g), chloroacetyl chloride (113 g) and methylene chloride (750 mL) at room temperature. Under stirring, anhydrous aluminum trichloride (147 g) was added in batches. After the addition was complete, the reaction mixture was heated to reflux and maintained for 3 hours to ensure complete reaction. Upon completion of the reaction, the mixture was quenched by carefully pouring it into ice water. Subsequently, the organic and aqueous phases were separated. The organic phase was washed sequentially with deionized water (500 mL x 2) and saturated sodium bicarbonate solution (500 mL x 2) to remove acidic impurities. The washed organic phase was dried with anhydrous sodium sulfate and filtered to remove the desiccant. The filtrate was concentrated by rotary evaporation and petroleum ether (1200 mL) was added to the residue. The mixture was cooled to room temperature and placed in a refrigerator overnight to promote crystallization. The following day, the crystallized product was collected by filtration and washed with a small amount of cold petroleum ether. Ultimately, the product was dried under vacuum to give 2,2',4'-trichloroacetophenone (193 g, 86% yield) in the form of an off-white solid.

References