Phase transfer catalyzed reaction of disodium salt of 1,3-dihydroxybenzene with propargyl bromide in solidliquid biphasic condition

In the present work, the reaction between disodium salt of 1,3-dihydroxybenzene (in situ formation) and propargyl bromide was carried out in a solid-liquid biphasic phase transferring catalytic system at 50 °C. Higher selectivity of the bis-derivative (1,3-bis(prop-2-ynyloxy)benzene) was obtained under solid-liquid PTC condion. The conversion of propargyl bromide to more than 99% was achieved in the presence of tetra-n-butylammonium bromide (TBAB) as PTC catalyst. From the experimental evidence, no mono-derivative was observed. Experiments were conducted to increase the conversion of propargyl bromide such as, stirring speed, various PTCs, temperature, various solvents and amount of TBAB loading. All the experiments were conducted to obey pseudo-first order rate law. Apparent activation energy was also determined from the Arrhenius plot.