Xanthene → 2,7-Bis(4-chlorobutyryl)xanthene

Participants

Reaction Conditions

Reaction Steps

To a mixture of 91.1 g (0.5 mole) xanthene, 176.3 g (1.25 moles) of 4-chlorobutyryl chloride and 3 liters of dried methylene chloride cooled to -20°C. was added slowly over 1/2 hour 146.7 g (1.1moles) of aluminum chloride, maintaining a temperature below -10°C. The reaction mixture was allowed to warm slowly to room temperature and then refluxed for 4 hours and cooled to room temperature. The mixture was decomposed by pouring cautiously into 2 liters of ice water, and the layers were separated. The aqueous layer was extracted again with methylene chloride. The methylene chloride layers were combined and evaporated to a small volume and cooled. The resulting solid was filtered off and recrystallized from acetone to give the desired product. M.P. 131°-132°C.

Provenance & Evidence