Base‐catalyzed hydroxymethylation of phenol by aqueous formaldehyde. Kinetics and mechanism

The effects of formaldehyde and hemiformal equilibria on the rates of the base‐catalyzed and hydroxymethylations of phenol by aqueous formaldehyde have been treated quantitatively. A kinetic model treating all seven simultaneous, parallel, consecutive, and competing reactions, as well as the equilibria, has been shown to apply to a wide variety of the conditions and to data from other works. Concentration‐induced solvent effects on the rates and on the ortho/para ‐substitution patters have been studied. The temperature dependence of the rate constants, both for dilute systems and systems composed primarily of phenol and aqueous formaldehyde, has been determined.