Kinetics and mechanism of the alkylation of phenol with cyclohexene in the presence of aluminum phenolate

The kinetics of the alkylation of phenol with cyclohexene in the presence of aluminum phenolate was studied. A mechanism is proposed for the ortho-alkylation of phenols by olefins, involving the intermediate formation of the ion pair (Al(OPh)/sub 4/)/sup -/R/sup +/ at a steady concentration. The ion pair is transformed into the o-alkylphenol in the controlling stage. The alkylation rate of phenol is higher than that of 2-cyclohexylphenol, and this is due to the determining effect of the entropy factor.