T. Crowell, E. H. Braue, P. Hillery
1984
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Abstract
Methyl 3,5-dihydroxybenzoate, like many polyhydroxy compounds, is soluble in molten potassium thiocyanate and in the eutectic Na+K+SCN“ , and reacts by nucleophilic attack of thiocyanate ion on the methyl group. The rate of this solvolysis for the ethyl ester is only 0.02 times that of the methyl at 150°C. Methyl 2,4-dihydroxybenzoate decarboxylates subsequently to displacement but the kinetics show no catalysis by the neighboring hydroxyl group.