Boron trifluoride etherate → 9,10-Dihydro-9,10-anthracenedicarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.1 ml. of boron trifluoride etherate in 40 ml. of ether and 2.0 g. of potassium carbonate is stirred at 0° C. for 10 minutes. A solution of 500 mg. of dispiro[oxirane-2,9'(10'H)-anthracene-10',2"-oxirane] in 20 ml. of ether is added. The resulting mixture is stirred at 0° C. for an additional 2 minutes, and filtered. The ether filtrate is washed twice with a mixture of 10 ml. of saturated sodium bicarbonate solution and 10 ml. of ice-water, then dried over anhydrous sodium sulfate and filtered. The ether is removed and the residue is recrystallized from ether/hexane to give 384 mg. of the desired product as yellow crystals, m.p. 132°-135° C.

Provenance & Evidence