Hydrogen Peroxide → 2,7-Diacetyloxyfluorene

Participants

Reaction Steps

Acetic anhydride (26.2 g) and 88% formic acid (68 g) were added in order to a mixture of 2-acetyl-7-acetoxyfluorene (45 g) and dichloromethane (450 mL). 36M-sulfuric acid (9 mL) was slowly added thereto at 9° C., and then a 34% hydrogen peroxide aqueous solution (25.9 g) was added to obtain a ocherous reaction mixture. This reaction mixture was refluxed for 9 hours by heating, and then it was cooled down to a room temperature and poured into water. The mixture was neutralized with saturated sodium hydrogencarbonate, and then the organic layer was sufficiently washed with 10% sodium hydrogensulfite to remove unreacted peroxide. The separated organic layer was concentrated under reduced pressure, and the resulting residue was purified by means of column chromatography (silica gel, eluting solvent: ethyl acetate) to obtain 2,7-diacetyloxyfluorene (22.5 g) of colorless crystal. Melting point: 167.6-168.3° C.

Provenance & Evidence