Acetophenone → 1-Phenylethanol

Participants

Reaction Steps

24.4 mg of [Ir(PPEI)COD]+ClO4- (+) (4×10-5 moles) (PPEI=2-pyridinal-phenylethylimine; COD=cis cis 1-5 cyclooctadiene), suspended in 1 ml of isopropanol were oxidized with air for 4 hours. The resulting yellow solution was degasified for 20 minutes at reflux in a nitrogen stream and treated with 3.75 ml of a deaerated isopropanol solution of KOH (8 mg of KOH). After a 30-minutes reduction in a nitrogen stream, 4.8 ml of deaerated acetophenone were added. After a 120-minute reaction, a conversion to 1-phenylethanol (+) of 91.2% and an e.e. of 13.6% were obtained. The polarimetric determination was effected on the hydrogenation product distilled at reduced pressure. Ratios:

Provenance & Evidence