1,2-Dichloroethane → (3S)-3-hydroxy-3-phenylpropanenitrile

HRID 846342Notes

Reaction equation

HRID 846342 reaction equation
[CH2:1]1[O:9][C@@H: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.[OH-].[K+]>[C:3]1([C@@H: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 9032Potassium CyanideHCID 114705(+)-Styrene oxide

Product 1

HCID 11084031(3S)-3-hydroxy-3-phenylpropanenitrileYield 33.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 14797Potassium HydroxideSolvent2×

Procedure

To a 250 round bottom flask were sequentially added 10.0 g of (R)-styrene oxide, 40 ml of 1,2-dichloroethane, 40 ml of 1N potassium hydroxide, 5.96 g of potassium cyanide and 267 mg of tetrabutylammonium bromide. The resulting mixture was heated at reflux for 6 hours. The reaction mixture was cooled and diluted with 1N potassium hydroxide, and extracted with diethyl ether. The ether extracts were combined and washed twice with a saturated sodium chloride solution. The organics layer was dried over magnesium sulfate and concentrated in vacuo. The resulting yellow oil was vacuum distilled at 13 mm pressure and the distillate collected at 140°-180° C. providing 4.11 g of title intermediate.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 6 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with diethyl ether
  5. washwashed twice with a saturated sodium chloride solution
  6. dry with materialThe organics layer was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. distillationdistilled at 13 mm pressure
  9. distillationthe distillate collected at 140°-180° C.

Sources & evidence

ORD record
ord-4fef408e975942a0bf95876d60ab7f67
Source dataset
uspto-grants-1992_08
Patent number
US05136079

Reaction notes

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