Hydrochloric Acid → 2-Nitro-4-(2-phenylpropan-2-yl)aniline

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Reaction Steps

To 510 parts of 36% w/w hydrochloric acid containing 170 parts of anhydrous zinc chloride, are added 690 parts of o-nitroaniline. This mixture is heated to reflux temperature and, over the next hour, 708 parts of α-methylstyrene are added with stirring. On completing the addition, the reaction mixture is maintained at reflux for a further one and a half hours before being poured, whilst still hot, into a solution of 600 g sodium hydroxide in 1400 parts of water. The mixture is stirred until cool and then 1500 parts of ether are added and the resulting two phases are passed through a fibre filter to remove a small quantity of suspended solids. The filtrate is transferred to a separator and the lower aqueous phase is run off and discarded. The organic phase is washed with 2×500 parts of water, dried over magnesium sulphate, treated with decolouring charcoal and filtered. The filtrate is concentrated on a steam-bath until the residue weighed approximately 2000 parts. It is diluted with 2000 parts of 40°-60° C. petroleum-ether and set aside to crystallise overnight. The product following filtration is suspended in 1500 parts of 40°-60° petroleum-ether, stirred for 1 hour, and filtered to yield 4-cumyl-2-nitroaniline as an orange crystalline solid with a m.p. 92°-3° C. and a purity of 100% by G.L.C. analysis.

Provenance & Evidence