Acetic Acid → 2-(4-hydroxyiminocyclohexa-2,5-dien-1-ylidene)-2-(4-methoxyphenyl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

80 g of KOH are dissolved in 400 ml of methanol and heated up to 55° C. To the solution are added 50 ml (0.37 mol) of p-methoxyphenylacetonitrile, followed by 35 ml (0.34 mol) of nitrobenzene. The reaction mixture is stirred at 55° C. for 4 hrs. After cooling, 500 ml of water are added with stirring. The resulting solution is acidified by addition of 110 ml of acetic acid in 100 ml of water, leading to a precipitate. The mixture is then filtered, and the solid is washed with a mixture of methanol and water. The crude product is dried in air and recrystallized from 500 ml of ethyl acetate. 45.6 g (53%) of (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-(4-methoxyphenyl)-acetonitrile are obtained in the form of orange crystals having a melting point of 161-163° C. (dec.).

Provenance & Evidence