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

HRID 1578037Notes

Reaction equation

HRID 1578037 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.N#N>[CH3:10][CH2:9][CH:8]([OH:11])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

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

Product 1

HCID 71471-Phenyl-1-propanol

Reagents, catalysts & solvents 2

HCID 947NitrogenSolventHCID 3776IsopropanolSolvent2×

Procedure

12.2 mg (2×10-5 moles) of [Ir(PPEI)COD]+ClO4- (+) were suspended in 50 ml of isopropanol and oxidized with air for 4 hours. The resulting solution was degasified for 20 minutes at reflux in N2 and then treated with 4.5 ml of a deaerated isopropanol solution of KOH (8 mg of KOH). The solution, after a preliminary 30-minute reduction in a nitrogen stream, was treated with 2.56 ml of deaerated propiophenone. After a 120-minute reaction, a conversion to phenylpropanol (+) of 93.3% with an e.e. of 26.1% was obtained. Ratios:

Workup

  1. waitThe resulting solution was degasified for 20 minutes
  2. waitThe solution, after a preliminary 30-minute reduction in a nitrogen stream
  3. customAfter a 120-minute reaction

Sources & evidence

ORD record
ord-34d1a0c1d1f2449ab9c4d4542dca1195
Source dataset
uspto-grants-1981_09
Patent number
US04290961

Reaction notes

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