Methanol → 2-Chloro-9H-fluoren-9-one

Participants

Reaction Steps

A methanol free, 40% solution of Triton B in pyridine (8 mL) was added to a stirred, room temperature solution of commercially available (Alpha) 2-chlorofluorene (17) (42 g, 0.21 mmoL) in pyridine (257 mL) and oxygen was bubbled through the mixture at a moderate rate for 18 h. The majority of the pyridine was then removed on the rotary evaporator at reduced pressure and 5% aqueous hydrochloric acid (500 mL) was added to the residue. The solid was collected by filtration and washed with 5% aqueous hydrochloric acid and water. After drying, the solid was extracted repeatedly with hexane to remove some hexane insoluble impurities. Evaporation of the hexane left 42.7 g(95%) of 2-chloro-9-fluorenone: mp 110°-113° C.

Provenance & Evidence