Hydroquinone → 2-Norbornanecarbonitrile

Participants

Reaction Conditions

Reaction Steps

159 g (3 moles) of acrylonitrile were dissolved in 100 ml of benzene and warmed to 50°C. after adding a pinch of hydroquinone. 196 g (3 moles) of cyclopentadiene were added dropwise at this temperature, with intensive stirring. In the course thereof, the temperature of the reaction mixture rose (it should not exceed 70°C.). After the exothermic reaction had subsided, the mixture was stirred for 1 hour at 80°C. The solvent was then distilled off and the residue was rectified in vacuo. This gave 272 g (76% of theory) of 2-cyano-bicyclo[2,2,1]heptene-5 of boiling point 82°-87°C/15 mm Hg.

Provenance & Evidence