The enzymatic hydrolysis of the meso-diester cis-eyelohex-4-ene-1,2-dicarboxylate to the monoester methyl-hydrogen(1S,2R)-cyclohex-4-ene-1,2-dicarboxylate using pig liver esterase has been studied both experimentally and theoretically. A chiral monoester product of high pharmaceutical interest is obtained with an enantiomeric excess of 97%. The enzymatic conversion of the meso-diester compound highly soluble in organic solvents to the desired monoester highly soluble in aqueous phase was studied in a two-phase contactor under controlled hydrodynamic conditions and interfacial contact area. A comprehensive mathematical model comprising mass transfer and simultaneous enzymatic conversion was developed. This model proved to be a simple and useful tool, making it possible to simulate the process under different conditions and to optimize the most relevant operating parameters, without resorting to exhaustive laboratory studies.