4-Methoxybenzenesulfonyl chloride → alpha-(4-Methoxyphenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

Participants

Reaction Steps

As described under 1.2., 10.3 g (0.05 mol) of α-hydroxyimino-3,4-dimethoxybenzyl cyanide are reacted with 11.37 g (0.055 mol) of 4-methoxyphenylsulfonic acid chloride in the presence of 7.6 g of triethylamine. After recrystallisation of the crude product from ethyl acetate/hexane, 3.26 g (17%) of α-(4-methoxy-phenylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide are obtained in the form of yellowish crystals having a melting point of 161-167° C. The 1H-NMR spectrum of the compound shows that it is a pure stereoisomer. The UV spectrum (acetonitrile) of the substance shows a broad absorption band with a maximum at 349 nm (ε=11700) that extends to 435 nm. Elemental analysis: C17H16N2O6S (376.38)

Provenance & Evidence