Acetic Acid → 4-(4-Chlorophenyl)-4-oxobutanenitrile

HRID 1723164Notes

Reaction equation

HRID 1723164 reaction equation
[C-]#N.[Na+].[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.[C:13](#[N:16])[CH:14]=[CH2:15].C(O)(=O)C>CN(C)C=O.O>[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([C:9](=[O:10])[CH2:15][CH2:14][C:13]#[N:16])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 7855AcrylonitrileHCID 8929Sodium Cyanide

Product 1

HCID 5873524-(4-Chlorophenyl)-4-oxobutanenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of freshly ground sodium cyanide (0.75 g, 15.0 mmol) in dimethylformamide (DMF) is added, over 30 min., 4-chlorobenzaldehyde (21.0 g, 150.0 mmol) in DMF. 30 Minutes after the addition is completed, acrylonitrile (5.96 g, 7.4 ml, 112.5 mmol) is added over a period of 1 hour. The mixture is stirred at RT for 3 hours, after which acetic acid (0.99 g, 0.94 ml, 16.5 mmol) is added. After 5 min., the reaction mixture is poured into water and extracted with chloroform. The combined chloroform layers are washed with water and with brine, dried and stripped of solvent. The residue is recrystallized and filtered to give 4-(4-chlorophenyl)-4-oxobutyronitrile.

Workup

  1. additionis added, over 30 min.
  2. addition30 Minutes after the addition
  3. waitAfter 5 min.
  4. extractionextracted with chloroform
  5. washThe combined chloroform layers are washed with water and with brine
  6. customdried
  7. customThe residue is recrystallized
  8. filtrationfiltered

Sources & evidence

ORD record
ord-b457da62283d426aa6d99cf9c8ee5a52
Source dataset
uspto-grants-1989_08
Patent number
US04859699

Reaction notes

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