Water → 2,4,6-Trichloroaniline

Participants

Reaction Steps

The procedure was repeated using a mixture of 20% water and 80% ethanol as the solvent instead of the anhydrous ethanol used above. This time the yield of 3-acetamido-1-(2,4,6-trichlorophenyl)-2-pyrazolin-5-one was very poor, i.e., only 8%, while a 57% yield of 2,4,6-trichloroaniline was obtained. This illustrates that, in contrast to the excellent yields produced in an organic medium, very poor yields are obtained when the rearrangement is run in an aqueous medium.

Provenance & Evidence