1-Phenyl-1-propanone → 1-Phenyl-1-propanol

HRID 1578034Notes

Reaction equation

HRID 1578034 reaction equation
Cl([O-])(=O)(=O)=O.[OH-].[K+].[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])[CH2:9][CH3:10]>C(O)(C)C>[CH3:10][CH2:9][CH:8]([OH:11])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 14797Potassium HydroxideHCID 123351Perchlorate

Product 1

HCID 71471-Phenyl-1-propanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

24.4 mg (4×10-5 moles) of [Ir(PPEI)COD]+ClO4- (-) suspended in 100 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 1.94 ml of an isopropanol solution of KOH (4 mg of KOH). After a 30-minute reduction in a nitrogen stream, 5.3 ml of deaerated propiophenone were added. After a 240-minute reaction, a conversion to phenylpropanol (-) of 98.5% with an e.e. of 25.07% was 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 240-minute reaction

Sources & evidence

ORD record
ord-efbbddcd1c5e40959ae16a0857e520ec
Source dataset
uspto-grants-1981_09
Patent number
US04290961

Reaction notes

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