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Asymmetric hydrolysis of (±)-l,2-diacetoxy-3-chloropropane (1) with a very small amount of a lipoprotein lipase gave {S)-\ of90% enantiomeric excess (e.e.). Reactions of (S)-l with phenols in an alkaline condition yielded the corresponding (5)-3-aryloxy-l,2-propanediols. From (S)-3-(lnaphthoxy)-l,2-propanediol (5) was synthesized the optically pure (*S)-isomer of propranolol [1isopropylamino-3-(l-naphthoxy)-2-propanol] (9), one of the jS-adrenergic blocking agents.