Acetic Acid → (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-thiophen-2-yl-acetonitrile

Participants

Reaction Steps

9.5 g of KOH are dissolved in 50 ml of methanol. To the solution are added 5 g (41 mmol) of thiophene-2-acetonitrile followed by 4.2 ml (41 mmol) of nitrobenzene. After the reaction mixture is stirred at room temperature for 2 hrs, 200 ml of water are added with stirring. The resulting solution is acidified by addition of 30 ml of acetic acid in 25 ml of water, leading to a dark orange precipitate. The mixture is then filtered, and the solid is washed with a mixture of methanol and water, and methanol. The crude product is dried in air and recrystallized from toluene. 4.7 g (50%) of (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-thiophen-2-yl-acetonitrile are obtained in the form of a dark orange powder having a melting point of 151-155° C. (dec.).

Provenance & Evidence