Water → 3-(2,6-Dichlorophenyl)propanenitrile

HRID 1026623Notes

Reaction equation

HRID 1026623 reaction equation
[C:1]([CH:3]([CH2:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])C(O)=O)#[N:2].O>CC(N(C)C)=O>[Cl:14][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:15])[C:8]=1[CH2:7][CH2:3][C:1]#[N:2]

Participants

4

Reactant 2

HCID 962WaterHCID 135607172-Cyano 3-(2,6-dichlorophenyl)propanoic acid

Product 1

HCID 126899803-(2,6-Dichlorophenyl)propanenitrileYield 94%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

2-Cyano-3-(2,6-dichlorophenyl)propanoic acid (447 mmol, 109 g) was dissolved in DMA (179 ml) and heated for 2 hours at 150° C. After cooling, the reaction mixture was poured into water and extracted with ether. The organic layer was washed with a saturated solution of sodium hydrogen carbonate and then with a saturated solution of sodium chloride. The organic phase was dried over sodium sulfate and concentrated under reduced pressure to afford 3-(2,6-dichlorophenyl)propanenitrile (94% yield, 83.8 g).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. washThe organic layer was washed with a saturated solution of sodium hydrogen carbonate
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0727394fb1744a89acb9bcbf33ed394
Source dataset
uspto-grants-2014_05
Patent number
US08729274B2

Reaction notes

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