Acetic Acid → HCID 21320295, compound

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Reaction Steps

The product of step A is dissolved in 100 ml. of acetic acid, 3.3 g. of itaconic acid is added followed by 2.3 g. of dinitrogen tetraoxide in 10 ml. of acetic acid (the latter being added dropwise). After two hours, the mixture is poured into water and extracted with diethyl ether. The ether extracts are washed with dilute sodium bicarbonate solution, with saturated sodium chloride solution, then dried. Evaporation provides a solid which is dissolved in chloroform and chromatographically fractionated on silica gel, eluting with chloroform-carbon tetrachloride, then chloroform. The desired product elutes slowly with chloroform. It is washed with hot hexane, then recrystallized from a hexane-chloroform mixture to provide 5-methylsulfinylmethyl-2-nitro-3-phenylbenzofuran, m.p. 161°-163° C. This is the product of Example 19.

Provenance & Evidence