Potassium Hydroxide → 3-(4-Fluorobenzylidene)bicyclo[2.2.2]oct-5-en-2-one

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Reaction Steps

A solution of bicyclo[2.2.2]oct-5-en-2-one (J. Oro. Chem. 33, 2211 (1968)) (3.34 g, 27.4 mmoles), 4-fluorobenzaldehyde (3.08 ml, 28.7 mmoles) and KOH (2 pellets) in 10 ml of 2-propanol was heated at 60° C. for 1.5 hours, cooled to room temperature and diluted with H2O and ether. The organic layer was washed with H2O, 2% aqueous HCl, saturated NaHCO3 and brine and dried (MgSO4). Removal of the volatiles in vacuo provided a residue which was recrystallized with hexanes. mp 85°-86° C.

Provenance & Evidence