1,2-Dichloroethane → 3-Hydroxy-3-phenylpropanenitrile

HRID 846343Notes

Reaction equation

HRID 846343 reaction equation
[CH2:1]1[O:9][CH:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.ClCCCl.[C-:14]#[N:15].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:3]1([CH:2]([OH:9])[CH2:1][C:14]#[N:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 7276Styrene OxideHCID 9032Potassium Cyanide

Product 1

HCID 865243-Hydroxy-3-phenylpropanenitrile

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

The procedure of Experiment 1 was repeated employing 1.0 g of racemic styrene oxide, 4 ml of 1,2-dichloroethane, 2 ml of water, 596 mg of potassium cyanide, and 267 mg of tetrabutylammonium bromide. After 6 hours of heating at reflux, the reaction mixture was cooled and worked up extracting with methylene chloride. Proton nuclear magnetic resonance analysis indicated the desired product contaminated with the phase transfer catalyst.

Workup

  1. temperatureAfter 6 hours of heating
  2. temperatureat reflux
  3. temperaturethe reaction mixture was cooled
  4. extractionworked up extracting with methylene chloride

Sources & evidence

ORD record
ord-c201372b795a439796f5ddf38bd5454f
Source dataset
uspto-grants-1992_08
Patent number
US05136079

Reaction notes

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