tThe effect of the reaction parameters water activity and reaction solvent was investigated for the dynamickinetic resolution (DKR) of rac-benzoin with immobilized Lipase TL as biocatalyst for transesterificationand the heterogeneous chemo-catalyst Zr-TUD-1 (Si/Zr = 25) for in situ racemization. Overall dry reactionconditions led to the best results for both catalysts. The immobilized lipase in a more environmentallybenign solvent like cyclopentyl methyl ether (CPME) exhibited a 1.6-fold higher activity and an up to1.5-fold higher half-life time than in the standard solvents such as toluene and 2-methyltetrahydrofuran(2-MeTHF). Among a variety of deep eutectic solvents (DESs) choline chloride:isosorbide (ChCl:Iso) wasfound to be suitable for the reaction system. The activity was lower than in the aforementioned solvents, but the very low solubility of the product (S)-benzoin butyrate in ChCl:Iso compared to the investigatedorganic solvents possesses great potential with respect to downstream processing. Optimized reactionparameters (dry CPME) were applied for DKR in batch and continuous mode yielding comparable orslightly better results than in toluene or 2-MeTHF.