Novel soluble "multi-site" phase transfer catalyst viz.1,3,5-tris(4-(2,2 -bis(N-triethylammoniummethylene chloride)eth-1-ene)phenoxymethyl)benzene (TBTEAPB) was synthesized and characterized by different spectral techniques such as FT-IR, 1 H NMR, 13 C NMR, MALDI-TOF mass and chloride ion analysis. The catalytic potential of this new multi-site TBTEAPB phase transfer catalyst was demonstrated by the C-alkylation of ␣-pinene with epichlorohydrin using low concentration of base (20% NaOH) at 40 • C. The pseudo-first order rate constants were calculated by following the disappearance of ␣-pinene through gas liquid chromatography. The efficiency of TBTEAPB catalyst was also studied by comparing the rate constants of reaction facilitated by single and di-site PTCs in a similar catalytic environment. The observed rate constants were found to be ∼ =6 and 3 times higher for the TBTEAPB multi-site PTC than for the single and di-site PTCs. Thorough kinetics of the reaction was also studied by varying the experimental parameters such as stirring speed, [catalyst], [substrate],
[NaOH] and temperature. Thermodynamic parameters of the reaction were also evaluated from the Arrhenius plot and the values are as follows; 7.12, -33.66, 13.46 and 0.41 kcal mol -1 for E a , S # , G # and H # , respectively. Based on the kinetic and thermodynamic parameters, we have proposed an hydroxide ion extraction mechanism.