The factors that influence the rate of alkylation of phenol under phase transfer catalysis (PTC) have been investigated in detail. Six linear, symmetrical tetraalkylammonium cations, Me4N+, Et4N+,(n-Pr) 4N+,(n-Bu) 4N+,(n-Hex) 4N+, and (n-Oct) 4N+, were examined to compare the effects of cationic radius and lipophilicity on the rate of alkylation. Tetraalkylammonium phenoxide· phenol salts were prepared, and their intrinsic reactivity ...
