Hydrochloric Acid → 4,4-Bis(p-fluorophenyl)cyclohexanone

Participants

Reaction Steps

To a stirred and cooled (ice-bath) mixture of 50 parts of fluorobenzene and 4.1 parts of 4-(4-fluorophenyl)-4-hydroxycyclohexanone were added portionwise 11 parts of aluminium chloride. Upon completion, stirring was continued for 2 hours while still cooling. The reaction mixture was decomposed by pouring onto a mixture of crushed ice and a hydrochloric acid solution. The product was extracted with methylbenzene. The extract was washed with water till neutralization, dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 4.3 parts (75.9%) of 4,4-bis(4-fluorophenyl)-1-cyclohexanone as a residue (intermediate 19).

Provenance & Evidence