Hydrochloric Acid → 3-Isopropylaniline

Participants

Reaction Steps

2 G. (0.127 mole) of 3-isopropylnitrobenzene is dissolved in 300 ml. of 50% aqueous ethanol and 23 g. of iron powder is added with good stirring. The reaction mixture is brought to reflux and 13.5 ml. of a solution of 5.2 ml. of concentrated hydrochloric acid in 25 ml. of 50% aqueous ethanol is added while maintaining reflux and stirring. After 1/2 hour of stirring, the reaction mixture is made basic with 2.5 N sodium hydroxide and steam distilled. The distillate is extracted with chloroform and the chloroform layer dried and concentrated by distillation through a short vigreau column under atmospheric pressure. The residue is vacuum distilled. One fraction with boiling point of 117°-118° C. at 18 mm. Hg. contains 15.14 g. of 3-isopropylaniline which is suitable for use in the next step without further purification.

Provenance & Evidence