Hydrochloric Acid → 6-Nitro-2-toluonitrile

참여 물질

반응 단계

A solution of 16 g (150 mmol) of n-butyl nitrite (97% pure) and 7.7 g (50 mmol) of 3-nitro-o-xylene (97% pure) in 50 ml of dimethylformamide is cooled to from −5 to −10° C., and a solution of 11 g (100 mmol) of potassium tert-butoxide in 50 ml of dimethylformamide is added dropwise at this temperature, over a period of 1.5 hours. The reaction mixture is stirred at room temperature for another 6 days. For work-up, the mixture is poured into ice-water, the pH is adjusted to 1 using hydrochloric acid and the aqueous phase is extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate and concentrated. This gives 8.2 g of product. The 2-methyl-6-nitrobenzonitrile can be purified by silica gel chromatography using toluene as mobile phase. M.p.: 101-103° C.

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