Acetophenone → 1-Phenylethanol

HRID 1578033Notes

Reaction equation

HRID 1578033 reaction equation
Cl([O-])(=O)(=O)=O.C1(CCN=CC2C=CC=CN=2)C=CC=CC=1.[OH-].[K+].[C:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])[CH3:25]>C(O)(C)C>[C:27]1([CH:24]([OH:26])[CH3:25])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 7410AcetophenoneHCID 14797Potassium HydroxideHCID 123351PerchlorateHCID 15790389HCID 15790389, compound

Product 1

HCID 74091-Phenylethanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

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:

Workup

  1. waitThe resulting yellow solution was degasified for 20 minutes
  2. temperatureat reflux in a nitrogen stream
  3. customAfter a 120-minute reaction

Sources & evidence

ORD record
ord-161023003ea54af9839e09d71c01f716
Source dataset
uspto-grants-1981_09
Patent number
US04290961

Reaction notes

Loading…