Potassium Cyanide → HCID 23442232, compound

HRID 2119433Notes

Reaction equation

HRID 2119433 reaction equation
[C-:1]#[N:2].[K+].[C:4]1([C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH2:13][CH3:14])[CH:11]=[O:12])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.C1COCC1>[OH:12][CH:11]([C:10]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:13][CH3:14])[C:1]#[N:2]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 17946111HCID 17946111, compound

Product 1

HCID 23442232HCID 23442232, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

17.4 g (91.6 mmol) of p-toluenesulfonic acid H2O, and then 5.9 g (91.6 mmol) of KCN in 25 ml of water, were added at 35° C. to a solution of 19.09 g (84.8 mmol) of 2,2-diphenylbutyraldehyde in 97 ml of THF (abs.). The mixture was then stirred at 40° C. for 4 hours and at room temperature for 16 hours. The mixture was evaporated to 1/3 of the volume, water was added, and the phases were separated. The aqueous phase was then extracted three times with ethyl acetate, and the combined organic phases were washed with 10% strength sodium disulfite solution, dried over MgSO4 and concentrated under reduced pressure. The crude product was chromatographed on silica gel with n-heptane/acetic acid (20:1). 19.5 g (92%) of 2-hydroxy-3,3-diphenylvaleronitrile were obtained as a pale oil.

Workup

  1. customThe mixture was evaporated to 1/3 of the volume, water
  2. additionwas added
  3. customthe phases were separated
  4. extractionThe aqueous phase was then extracted three times with ethyl acetate
  5. washthe combined organic phases were washed with 10% strength sodium disulfite solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was chromatographed on silica gel with n-heptane/acetic acid (20:1)

Sources & evidence

ORD record
ord-70d5d9c4d90c426392c88b5938829e92
Source dataset
uspto-grants-2004_02
Patent number
US06686369B1

Reaction notes

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