The preparation of 2-nitro-1-naphthoic acid, and the alkaline hydrolysis of ethyl 2-nitro-1-naphthoate and ethyl 8-nitro-1-naphthoate in ethanol-water
Degree GrantorUniversity of Canterbury
Degree NameMaster of Science
Possible methods of the preparation of 2-nitro-1-nephthoic acid, a derivative of naphthalene which has not previously been synthesised, have been reviewed and it has been prepared from 2-nitro-1-methylnaphthalene. A mechanism has been proposed for the condensation of aromatic nitromethyl compounds with diethyl oxalate. Ethyl 2-nitro-1-naphthoate and ethyl 8-nitro-1-naphthoate have been prepared and the kinetics of their alkaline hydrolysis in ethanol-water (85:15 by weight) have been studied over the temperature range 50-60°C. In following the kinetics of hydrolysis, a conductivity method has been used. Energies and entropies of motivation have been calculated for these hydrolysis reactions. Certain anomalies in activation energy and entropy values for the alkaline hydrolysis of nitro substituted ethyl 1-naphthoates, compared with those obtained for nitro substituted ethyl benzoates, have been discussed.