p-Toluenesulfonic acid → HCID 15839203, compound

HRID 2119426Notes

Reaction equation

HRID 2119426 reaction equation
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH3:10])[C:8]#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=[O:24])=CC=1.[C-:28]#[N:29].[K+]>C1COCC1.O>[OH:24][CH:8]([C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:10])[C:28]#[N:29]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9032Potassium CyanideHCID 796772,2-Diphenylpropiononitrile

Product 1

HCID 15839203HCID 15839203, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

42.3 g (0.201 mol of 2,2-diphenylpropionitrile [sic] were dissolved in 230 ml of THF, and 41.4 g (0.217 mol) of p-toluenesulfonic acid were added. Then 14.09 g (0.217 mol) of KCN in 60 ml of water were added dropwise. The mixture was then heated at 40° C. for 3 hours. The reaction mixture was concentrated to about 30% under reduced pressure, taken up in water and extracted three times with ethyl acetate. The combined organic phases were washed twice with sodium disulfite solution, dried with MgSO4 and concentrated under reduced pressure. The crude product was chromatographed on silica gel with n-heptane/ethyl acetate (20:1). 41.2 g (86%) of 2-hydroxy-3,3-diphenylbutyronitrile were obtained.

Workup

  1. concentrationThe reaction mixture was concentrated to about 30% under reduced pressure
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic phases were washed twice with sodium disulfite solution
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was chromatographed on silica gel with n-heptane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-b87f53d694964e8fa907c0c3fecfdb4a
Source dataset
uspto-grants-2004_02
Patent number
US06686369B1

Reaction notes

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