Novel soluble "multi-site" phase transfer catalyst viz. 1.3,5-tris(4-(2,2'-bis(N-triethylammoiummethlene chloridewth-1-ene)phenoxymethyl)benzene (TBTEAPB) was synthesized and characterized by different spectral techniques' such as FT-IR. H-1 NMR, C-13 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 a-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 alpha-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 congruent to 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 is 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, Delta S*, Delta G* and Delta H*. respectively. Based on the kinetic and thermodynamic parameters, we have proposed an hydroxide ion extraction mechanism. (c) 2005 Elsevier B.V. All rights reserved.