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The solvolysis of 25 differently substituted chloromethylated phenols was studied kinetically in methanol at 25 °C. A sharp decrease of the initial reaction rate with in-creasing concentrations of added acids can be explained by a very fast solvolysis of the phenolate anions in comparison with the undissociated compounds. The latter show strictly first order kinetics up to high conversions and the rate constants can be partly correlated with the Jaffé relation. Highly negative values for the reaction constants q = -5.4 and q = -6.2 for ortho-and para-chloromethylated compounds show, that the undissociated phenols react according to the S N l -mechanism. However, deviations are found for compounds with strongly electron attracting substituents, which may be partly caused by an intramolecular catalytic effect of the phenolic hydroxy group in the case of the ortho-isomers.

Kinetische Untersuchung der Methanolyse von chlormethylierten Phenolen / Kinetic Studies of the Methanolysis Reaction of Chloromethylated Phenols