4-Nitrobenzaldehyde → Fluoreneone

Participants

Reaction Steps

Into a 200 ml round-bottom flask, 5.0 g of a fluorene compound (m.p. 205.5°-207.5° C.) having the following structural formula ##STR8## which had been obtained by reacting 2,7-di-t-butyl-4-chloromethylfluorene with triphenylphosphine and then condensing the reaction product with 4-nitrobenzaldehyde, was introduced together with 0.3 g of potassium hydroxide and 100 ml of pyridine. The resulting mixture was stirred at room temperature for 20 hours in an air atmosphere. After completion of the reaction, 200 ml of water was added to the reaction mixture, and the reaction product was extracted with methylene chloride. The resulting organic layer was dried with Na2SO4 and the solvent was then removed by evaporation under reduced pressure. The residue was purified with a silica gel short column (methylene chloride/hexane = 2/1). Thereafter, the solvent was removed by evaporation under reduced pressure and the residue was recrystallized from a mixture of ethyl acetate and ethanol, thereby obtaining 1.7 g (yield 33%) of a fluorenone compound having the following structural formula as a yellow powder. The melting point of this compound was 223°-224° C. ##STR9##

Provenance & Evidence