Maleic Anhydride → Bicyclo(2.2.2)oct-5-ene-2,3-dicarboxylic Anhydride

Participants

Reaction Steps

To a solution of maleic anhydride (10.30 g, 105.0 mmol) in toluene (100 mL) was added 1,3-cyclohexadiene (8.41 g, 105.0 mmol). The mixture was heated to reflux temperature and allowed to react for 3 hrs. After cooling to room temperature, the solvent was evaporated and the remaining solid was recrystallized from EtOAc/hexane to yield pure bicyclo[2.2.2]oct-5-en-2,3-dicarboxylic anhydride as colorless crystals: 14.11 g (75% yield), mp=117° C.

Provenance & Evidence