Methanol → 5-(4-nitrobenzylidene)-5H-dibenzo[a,d]cycloheptene

Participants

Reaction Conditions

Reaction Steps

To 150 ml of dimethylsulfoxide, 3.60 g (about 90 mmol) of oily sodium hydride (about 60%) was added at room temperature. After the addition, the mixture was heated to the inner temperature of around 70° C. in an oil bath, and stirred under the same conditions for 1 hour. Thereafter, the reaction solution was cooled to room temperature, and then a solution of 25.1 g (92 mmol) of the diethyl-4-nitrobenzyl phosphonate and 10.0 g (48.6 mmol) of 5H-dibenzo[a,d]cyclohepten-5-one in 50 ml dimethyl sulfoxide was added dropwise thereto. After the addition was completed, the resulting mixture was stirred for 15 minutes at room temperature, and thereafter heated and stirred for 2 hours in an oil bath while keeping its internal temperature at 70 to 80° C. After the reaction was completed, the reaction mixture was cooled to room temperature, and then poured in about 1 liter of saturated brine, followed by extraction with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. To the residue thus obtained was added methanol, and the precipitated crystals were collected by filtration. The crystals were then recrystallized using a methanol/acetone mixed solvent to obtain 10.94 g of 5-(4-nitrobenzylidene)-5H-dibenzo[a,d]cycloheptene. Yield: 69.3%; m.p.: 151.5 to 152.5° C.

Provenance & Evidence