Hydrochloric Acid → alpha-(4-Hydroxybenzenesulfonyloxyimino)thien-2-ylacetonitrile

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Reaction Steps

With vigorous stirring, a solution of 12 g of NaOH in 20 ml of water is added to a solution of 27 g (0.08 mole) of α-(4-acetoxybenzenesulfonyloxyimino)thienylacetonitrile (3c) in 125 ml of tetrahydrofuran. After 1 hour, the reaction mixture is acidified with 20% hydrochloric acid and, after the addition of water and diethyl ether, the phases are separated. The aqueous phase is extracted with ether, the combined organic phases are dried over MgSO4, and the solvent is distilled off. The residual crude product is recrystallised from toluene, affording 17 g of beige-coloured crystals which melt at 151°-152° C.

Provenance & Evidence