The lipase-catalyzed asymmetric alcoholysis of α-cyano-3-phenoxybenzyl acetate (CPBAc) in organic solvents for the synthesis of S-α-cyano-3-phenoxybenzyl alcohol (S-CPBA) was studied. With lipaseAlcaligenes sp. as catalyst, Tetrahydrofuran as solvent and methanol as acylacceptor, the effects of temperature, water content, rotation speed, the molar ratioof ester to alcohol and the addition amount of lipase on the reaction were investigated. The optimal conditions were determined as 35～45 ℃, addition of 0%～1% water, rotation speed of 200 r/min,molar ratio of ester to alcohol at 1:0.5 and addition of 10 mg/mL lipase whenthe concentration of CPBAc was 337.08 mmol/L. Then the inhibition of substrateand product on the reaction, the stability of the product and the reuse of the lipase were also studied. The reaction processes under different substrate concentrations were examined carefully. The results showed that the reaction could becarried out effectively even at the high substrate concentration of 200 g/L under the optimal conditions. After reaction for 33 h, the conversion of S-CPBAreached about 49%, and the ee of S-CPBA and R-CPBAc exceeded 98%and 95%, respectively. The reaction was scaled up and good result was also achieved.

Key words: α-cyano-3-phenoxybenzyl acetate, enzyme catalysis in organic media, asymmetric alcoholysis