Sodium Cyanide → 3-Benzoylpropionitrile

HRID 2189937Notes

Reaction equation

HRID 2189937 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C([O-])(=O)C.[K+].[C-:17]#[N:18].[Na+]>C(O)C.O>[O:5]=[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:2][C:17]#[N:18]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 702953-ChloropropiophenoneHCID 517044Potassium Acetate

Product 1

HCID 1384653-BenzoylpropionitrileYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 3-chloro-1-phenylpropan-1-one (5.0 g, 29.7 mmol) in hot ethanol (7 mL) was added potassium acetate (2.91 g, 29.77 mmol). After cooling to room temperature, the precipitated salt was removed via filtration. To the filtrate in a septum-sealed flask under a nitrogen bubbler was slowly added sodium cyanide (2.91 g, 59.3 mmol) as a solution in water (10 mL). After stirring at room temperature for 24 hours, ethanol (30 mL) was added, and the mixture was cooled in an ice bath. The precipitate was filtered and rinsed with ethanol to provide the product (3.42 g, 73%) as fluffy white solid.

Workup

  1. customthe precipitated salt was removed via filtration
  2. customTo the filtrate in a septum-sealed flask under a nitrogen bubbler was slowly added
  3. temperaturethe mixture was cooled in an ice bath
  4. filtrationThe precipitate was filtered
  5. washrinsed with ethanol

Sources & evidence

ORD record
ord-2eaa63fff7b54503a240798af339fe52
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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