Water → 2-Acetylfluorenon

Participants

Reaction Conditions

Reaction Steps

To a solution of 77.0 g (0.74 mol) of 2-acetylfluorene in 1.1 l of acetic acid are added at 90° C and under intense stirring, 385 g (1.3 mol) of sodium bichromate during a period of 1 hr to 1 hr 15 min. Thereupon, the reaction mixture is allowed to stand under the same conditions for 4 hours, then poured into 4.6 l of water heated to 90° C and kept overnight at room temperature. The precipitate is filtered off, washed with 900 ml of a 2-percent sulfuric acid till a colorless wash solution appears, and with water until the acid reaction disappears. Then the precipitate is treated under intense stirring, with 540 ml of a 5-percent caustic soda solution heated to 90° C, and let cool down to room temperature. The precipitate is filtered off, washed with water and dried in a drying cabinet at 80° C to obtain 62.5 g of crude 2-acetylfluorenone which is then recrystallized from 1.0 l of benzene for the sake of purity. The yield of 2-acetylfluorenone equals 55.5 g (68.0 wt% as calculated for 2-acetylfluorene or 50 wt.% when calculated for fluorene), m.p. 160°-161.5° C.

Provenance & Evidence