Acetic Acid → 2-(3,5-Dichlorophenyl)-3-oxobutyronitrile

HRID 1682467Notes

Reaction equation

HRID 1682467 reaction equation
[CH3:1][CH2:2][O-:3].[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([CH2:13][C:14]#[N:15])[CH:9]=[C:10]([Cl:12])[CH:11]=1.C(OCC)(=O)C.C(O)(=O)C>C(O)C.C(COC)OC.CCCCCC.O>[Cl:5][C:6]1[CH:7]=[C:8]([CH:13]([C:2](=[O:3])[CH3:1])[C:14]#[N:15])[CH:9]=[C:10]([Cl:12])[CH:11]=1

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2723922Sodium ethoxideHCID 126899782-(3,5-Dichlorophenyl)acetonitrile

Product 1

HCID 197051032-(3,5-Dichlorophenyl)-3-oxobutyronitrileYield 179.5%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8058HexaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of NaOEt (from 0.69 g sodium), in ethanol (25 ml) at reflux, was added over 5 minutes a mixture of 3,5-dichlorophenylacetonitrile (9.3 g) and ethyl acetate (3.3 g) in dry dimethoxyethane (10 ml). After stirring at reflux for 4 hours, the mixture was cooled on ice, acidified with acetic acid, poured into cold water and extracted with dichloromethane. The combined extracts were washed with water and concentrated to give an oil. Trituration with hexane gave 2-(3,5-dichlorophenyl)-3-oxobutyronitrile as a colourless solid (4.15 g).

Workup

  1. additionwas added over 5 minutes
  2. temperatureat reflux for 4 hours
  3. temperaturethe mixture was cooled on ice
  4. extractionextracted with dichloromethane
  5. washThe combined extracts were washed with water
  6. concentrationconcentrated
  7. customto give an oil

Sources & evidence

ORD record
ord-b4fb3005e9834dc797ba70d709491551
Source dataset
uspto-grants-1997_06
Patent number
US05635507

Reaction notes

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