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

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Reaction Steps

To 20.4 parts of 36% w/w hydrochloric acid in which had previously been dissolved 13.4 parts of anhydrous zinc chloride is added 27.6 parts of o-nitroaniline. This mixture is heated to reflux temperature and during the next hour 23.6 parts of α-methylstyrene are added dropwise with stirring. After completing the addition the reaction mixture is stirred and refluxed for further 2 hours before being poured whilst still hot into a solution of 50 parts sodium hydroxide in 100 parts of water. This mixture after stirring for 15 minutes is set aside to cool, whereupon the upper organic phase solidified. The solid cake is then broken up, filtered off, washed with water, dried, and crystallised from ethanol to give 4-cumyl-2-nitro-aniline as orange crystals m.p. 92°-4° C. with the following percentage composition by weight.

Provenance & Evidence