Nitrogen → 1-Phenyl-1-propanol

HRID 1578035Notes

Reaction equation

HRID 1578035 reaction equation
Cl([O-])(=O)(=O)=O.[OH-].[K+].N#N.[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])[CH2:11][CH3:12]>C(O)(C)C>[CH3:12][CH2:11][CH:10]([OH:13])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 71481-Phenyl-1-propanoneHCID 14797Potassium HydroxideHCID 123351Perchlorate

Product 1

HCID 71471-Phenyl-1-propanol

Reagents, catalysts & solvents 1

HCID 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 yellow limpid solution so obtained was degasified for 20 minutes at reflux under a nitrogen stream and then treated with 2.7 ml of a deaerated isopropanol solution of KOH (2 mg of KOH). The solution was preliminarily reduced for 30 minutes in a N2 stream at reflux and then treated with 2.56 ml of deaerated propiophenone. After 60 minutes the reaction was stopped, obtaining a conversion to phenylpropanol (+) of 57.3% with an e.e. of 30%. Ratios:

Workup

  1. customThe yellow limpid solution so obtained
  2. waitwas degasified for 20 minutes
  3. temperatureat reflux under a nitrogen stream
  4. temperatureat reflux
  5. waitAfter 60 minutes the reaction was stopped

Sources & evidence

ORD record
ord-9e73c4547a364ebbb8239f5e056fb5cd
Source dataset
uspto-grants-1981_09
Patent number
US04290961

Reaction notes

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