ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Kinetics and Mechanism of Alkali-Catalyzed Reaction of 2-MethyIresorcinol with Formaldehyde in Different Media

H. C. Malhotra, P. S. Jassal, and M. Jassal

Department of Chemistry, University of Delhi, Delhi-110007, India

Abstract: A comprehensive kinetic and mechanistic study of 2-methylresorcinol and formaldehyde has been carried out in the temperature interval 65-80°C using the different concentrations of sodium hydroxide as catalyst. The reaction follows an overall second-order rate law. Reaction proceeds with the formation of monomethylol 2-methylresorcinol in the first step and dimethylol 2-methylresorcinol in the second one. The overall rate constant k has been resolved into stepwise rate constants k₁ and k₂. The mechanism of reaction, based on ∆S and ∆E values, is also proposed. Effect of changing the nature of catalyst shows that the rate of the reaction gradually increases in the order ethylamine, diethylamine, triethylamine, tetraethylammonium hydroxide and attains maximum value with sodium hydroxide. Similarly as the dielectric constant of the solvent used increases, the rate of the reaction of 2-methylresorcinol with formaldehyde also increases and it is the highest with 1,4-dioxan and lowest when methanol was employed as solvent.

Full paper in Portable Document Format: 492a85.pdf

Chemical Papers 49 (2) 85–90 (1995)