MECHANISM AND KINETICS OF LIQUID-LIQUID PHASE TRANSFER CATALYZED ETHERIFICATION OF EUGENOL WITH ALLYL BROMIDE

摘要

4-allyl-1-allyloxy-2-methoxybenzene, an intermediate in the synthesis of bioactive dinaphthalene compounds, was synthesized from eugenol and allyl bromide by using tetra-n-butyl ammonium bromide under liquid-liquid phase transfer catalysis (L-L PTC) at 30℃. Along with the desired O-alkylation product, C-alkylation product was also formed in traces. Suitable reaction mechanism was proposed and kinetic model developed. Effect of various reaction parameters on the conversion and selectivity was studied in detail. The reaction follows the pseudo-first-order kinetics. Use of stoichiometrically deficient quantity of NaOH resulted in the formation of O-alkylation product with high selectivity.