Dimethyl Sulfoxide → 4,4'-[Naphthalene-2,7-diylbis(oxy)]di(benzene-1,2-dicarbonitrile)

Participants

Reaction Steps

A mixture of 4.0 g (0.025 mol) of 2,7-dihydroxynaphthalene (2.2 g, 0.054 mol) of 50% aqueous sodium hydroxide, 30 ml of dimethyl sulfoxide and 25 ml of benzene was heated at reflux under a nitrogen atmosphere for 4 hours. The water was azeotroped from the mixture with a Dean-Stark trap. The reaction content was cooled to room temperature and 8.7 g (0.05 mol) of 4-nitrophthalonitrile was added in one sum. The resulting mixture was stirred for 15 hours at room temperature and was then poured into 150 ml of water. The light-brown precipitate was collected by suction filtration, washed with water, dried at reduced pressure, and washed with hot absolute ethanol to yield 6.1 g (59%) of the desired product, m.p. 201°-204° C.

Provenance & Evidence