The alkaline hydrolysis of the ethyl and methyl esters of 1-naphthoic acid and 2-naphthoic acid

Samples of the ethyl and methyl esters of 1-naphthoic acid and 2-naphthoic acid have been prepared and the kinetics of hydrolysis of these esters have been studied in alkaline solutions over the temperature range 30°C- 60°C. Aqueous methanol was employed as solvent for the methyl esters, and aqueous ethanol for the ethyl esters. Relative reactivities at the 1- and 2- positions as measured by this work are in line with theoretical prediction, and the relative rates of the methyl and ethyl esters have been discussed. Comments have been made on an earlier investigation by Bergmann and Hirshberg of the methyl compounds, the results of which appear to be anomalous. A value for the Hammet σ constant for the fused benzene ring has been derived and has been compared with values calculated by other investigators