Intramolecular alkylation of phenols. Part II. ortho-versus para- Alkylation

Abstract

4-(m-Hydroxyphenyl)butyl toluene-p-sulphonate was used, under basic conditions, as a model for investigating the factors which affect the ortho- : para-alkylation ratio of phenols. The ratio was sensitive to the nature of the solvent, the metal cation, salt effects, and temperature. The suggested mechanism underlines the importance of the nature of the association between the metal and phenoxide ions on the orientation of the reaction.