1,2-Dimethyl-3-nitrobenzene → 3-Methyl-5-nitrobenzaldehyde

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Reaction Steps

A mixture of nitroxylene (150 g), N-bromo succinimide (160 g) and benzoylperoxide (4.8 g) in carbontetrachloride (1200 ml) was heated to reflux for 4 hours with a mechanical stirrer. The precipitated succinimide was filtered and the filtrate evaporated. The oily residue was dissolved in chloroform (800 ml) and bistetrabutyl ammonium chromate (420 g) was added. The solution was refluxed for 3 hours, cooled to room temperature and diluted with benzene (500 ml) and filtered. The salts were washed with ethyl acetate until no desired material appeared on thin layer chromatography. The combined organic layer was evaporated and the residue, after chromatography, afforded the desired aldehyde in 50% yield. m.p. 81°-82° C.

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