Kinetics of the reaction of chloromethylated phenols with aniline and substituted anilines

Abstract

The kinetics of the reaction of several chloromethylated phenols with substituted anilines, mainly p-nitroaniline, were studied for dimethyl sulphoxide solution by conductivity measurements. Substitution of the chlorine atoms proceeds in two steps. In a reversible step hydrogen chloride is eliminated by a suitable base to form a quinone methide. The aniline is added to this intermediate in the second step, forming the anilinomethylphenol as the product. The base in the first step may be the solvent, if weakly basic anilines (e.g.p-nitroaniline) are used, or the aniline, if the reaction is carried out with more basic anilines (e.g. aniline itself).