Fluorene → HCID 1957070, compound

Participants

Reaction Steps

p-Chlorobenzoyl chloride (43.8 g.) was added dropwise to a stirred mixture of fluorene (41.5 g.) aluminum chloride (33.4 g.) and carbon disulphide (100 ml.). After the vigorous reaction had subsided the mixture was stirred and boiled under reflux for 6 hours. It was cooled, poured onto ice, the carbon disulphide distilled off on a steam bath, and the solid product filtered off, washed, dried and recrystallised from benzene to give 2-p-chlorobenzoylfluorene, m.p. 183° C. This was reacted by the method of Example 1 to give trans-1-(2-fluorenyl)-1-p-chlorophenyl-3-dimethylaminoprop-1-ene, hydrochloride from ethanol, m.p. 236°-237° C. Isomeric homogeneity was confirmed by n.m.r. spectroscopy.

Provenance & Evidence