The enantioselective esterification of (R,S)-ibuprofen has been performed with Novozym 435(TM) in solvent media under reduced pressure. The nature of the solvent affects the activity and enantioselectivity of the lipase. High esterification rates are obtained in solvents having high hydrophobicity (log P > 4). On the other hand, the best enantioselectivity is obtained with solvents having low hydrophobicity (log P < 3). This particular enantioselectivity trend is observed within the individual solvent families investigated (alkanes, ethers and aromatics).