P-Tolunitrile

Hydrolysis of />-Tolunitrile. As in the case of benzonitrile, alkaline h> drolysis is preferable to hydrolysis by 70% sulphuric acid. Boil a mixture of 5 g. of p-tolunitrile, 75 ml. of 10% aqueous sodium hydroxide solution and 15 ml. of ethanol under a reflux water-condenser. The ethanol is added partly to increase the speed of the hydrolysis, but in particular to prevent the nitrile (which volatilises in the steam) from actually crystallising in the condenser. The solution becomes clear after about i hour s heating, but the boiling should be continued for a total period of 1-5 hours to ensure complete hydrolysis. Then precipitate and isolate the p-toluic acid, CH3CgH4COOH, in precisely the same way as the benzoic acid in the above hydrolysis of benzonitrile. Yield 5 5 g. (almost theoretical). The p-toluic acid has m.p. 178°, and may be recrystallised from a mixture of equal volumes of water and rectified spirit. 

The crude substance may also be distilled under diminished pressure and the p-tolunitrile collected at 104-106 /20 uun. 

Hydrolysis may be effected with 10-20 per cent, sodium hydroxide solution (see p-Tolunitrile and Benzonitrile in Section IV,66) or with 10 per cent, methyl alcoholic sodium hydroxide. For diflScult cases, e.g., a.-Naphthoniirile (Section IV,163), a mixture of 50 per cent, sulphuric acid and glacial acetic acid may be used. In alkahne hydrolysis the boiling is continued until no more ammonia is evolved. In acid hydro-lysis 2-3 hours boiling is usually sufficient the reaction product is poured into water, and the organic acid is separated from any unchanged nitrile or from amide by means of sodium carbonate solution. The resulting acid is identified as detailed in Section IV,175. 

Nitro-p-tolunitrile Stannous chloride Sulfuric acid Ammonia... 

Preparation of 2-Nitro-4,4 -Dicyanostilbene 10 grams of 2-nitro-p-tolunitrile and 8.1 grams... 

The substance may be obtained from p-naphthylamine (Section IV,38) by the procedure described imder p Tolunitrile (Section IV,66). 

Evidence was provided for such an interpretation of the reaction by showing that. J/ -benzoylbenzimidoyl chloride (110) with p-tolunitrile reacted in the presence of stannic chloride to afford a 56% yield of the... 

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