In the present paper, we describe several pathways employing immobilized lipase from Candida antarctica B (CAL-B) as biocatalyst to prepare easily both enantiomers of 3-(1-hydroxyethyl)phenol. We have applied hydrolysis with Na2 CO3 in organic media under mild conditions. The reaction parameters solvent effect, amount of lipase, and Na2 CO3 were examined with 3-(1-acetoxyethyl)phenyl acetate as substrate. In alkaline hydrolysis, (R)-3-(1-hydroxyethyl)phenol was obtained with ee=99% and (S)-(-)-3-(1-acetoxyethyl)phenol with ee=98% at optimal conversion (c=50%) and high selectivity (E>200). Two other deacylation reactions were compared: alcoholysis with MeOH and with NEt3 . The acylation of 3-(1-hydroxyethyl)phenol with vinyl acetate was also examined. Alkaline hydrolysis gave the best results, while good regioselectivity and enantioselectivity were observed in alcoholysis and acylation reactions. Finally, (S)- and (R)-3-(1-hydroxyethyl)phenol (ee>98%), key intermediates for the synthesis of important drugs, were prepared from the corresponding racemic diacetate through alkaline hydrolysis.