Acetic Acid → (5-Hydroxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrile

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Reaction Steps

14 g of KOH are dissolved in 50 ml of methanol. To the solution are added 7.1 ml (62 mmol) of phenylacetonitrile followed by 10 g (62 mmol) of 2-nitrothiophene dissolved in 30 ml of methanol. After the reaction mixture is stirred in the ice bath for 10 min, 200 ml of water are added with stirring. The resulting solution is acidified by addition of 55 ml of acetic acid in 50 ml of water, and extracted with ethyl acetate. The organic phase is washed with sodium chloride solution, and dried over MgSO4. After the solvent is distilled off, the residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:3), and recrystallization from toluene. 5.3 g (38%) of (5-Hydroxyimino-5H-thiophen-2-ylidene)-phenyl-acetonitrile are obtained in the form of orange crystals having a melting point of 165° C. (dec.).

Provenance & Evidence