Ethanol → HCID 10513515, compound

HRID 846387Notes

Reaction equation

HRID 846387 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]#[N:11].[O-:12][CH2:13][CH3:14].[Na+].[Na].C(O)C>C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:13](=[O:12])[CH3:14])[C:10]#[N:11]

Participants

7

Reactant 4

HCID 702EthanolHCID 805662,4-DichlorophenylacetonitrileHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 10513515HCID 10513515, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,4-dichlorophenylacetonitrile (30.00 gms, 161 mmol) (Aldrich) in dry ethyl acetate (36 ml) was added dropwise to an ethanolic solution of sodium ethoxide, prepared in situ from sodium metal (4.90 g, 213 mmol) and dry ethanol (60 ml). This reaction mixture was refluxed for two hours, allowed to stand overnight at room temperature and the ethanol was evaporated. The yellow solid obtained was dissolved in water and the resulting solution was extracted twice with ether. The aqueous layer was chilled and acidified with hydrochloric acid. The crude product was extracted with ether to give 23.31 g of white solid.

Workup

  1. temperatureThis reaction mixture was refluxed for two hours
  2. customthe ethanol was evaporated
  3. customThe yellow solid obtained
  4. extractionthe resulting solution was extracted twice with ether
  5. temperatureThe aqueous layer was chilled
  6. extractionThe crude product was extracted with ether

Sources & evidence

ORD record
ord-801b6f38f5ff420cbe5907ad4430ba2f
Source dataset
uspto-grants-1992_08
Patent number
US05136080

Reaction notes

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