Water → bis(3,4-dichlorophenyl)methanone

Participants

Reaction Steps

Aluminum chloride (16 g.) was slurried with 1,2-dichlorbenzene (40 ml.). A solution of 3,4-dichlorobenzotrifluoride (21.5 g.) in 1,2-dichlorobenzene (40 ml.) was added to the aluminum chloride slurry over 1.25 hours. The solution became dark red and viscous. The reaction mixture was stirred for 88 hours at room temperature and then heated to 70° C. for 6 hours. The reaction contents were poured into water and the aqueous portion was extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate and filtered. The solvents were removed on a rotary evaporator (methylene chloride) followed by a bulb-to-bulb distillation to remove most of the dichlorobenzene (85° C., 10 torr). Aqueous ethanol (U.S. Industrial Chemical Company, special denatured ethanol, 10% water added, 100 ml. total) was added to the reaction product and the contents of the flask were refluxed overnight. The solution was allowed to cool and the solid was collected and washed with ethanol to give a whitish solid (25.7 g., 80% yield). An analytical sample was obtained by recrystallization from ethanol/toluene (3.5-1) mp =144.

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