Chloroform → HCID 19788804, compound

HRID 1656701Notes

Reaction equation

HRID 1656701 reaction equation
[C:1]1([C:7](=[CH:10][CH3:11])[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH:14]([Cl:17])(Cl)[Cl:15]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[Cl:15][C:14]1([Cl:17])[CH:10]([CH3:11])[C:7]1([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]#[N:9]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 29675738586-17-3

Product 1

HCID 19788804HCID 19788804, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

A three-neck flask was charged with a mixture of 20 g (0.14 mol) of 2-phenyl-2-butenonitrile, 200 g of chloroform and 2 g of triethylbenzylammonium chloride, and the mixture was stirred. To the mixture were dropwise added 100 g of a 50% sodium hydroxide solution under cooling with ice. The reaction mixture was further stirred at room temperature for 15 hours, then poured into ice water, and the organic phase was separated. The aqueous phase was extracted with hexane. The organic phase fractions were combined together, and dried over anhydrous sodium sulfate. The inorganic substances were filtered off, and the organic solvent was distilled off under a reduced pressure. The resultant oily residue was distilled under a pressure of 0.1 mmHg (116°-120° C.) to obtain 10.4 g of 2,2-dichloro-3-methyl-1-phenylcyclopropanecarbonitrile. Yield: 33%.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe reaction mixture was further stirred at room temperature for 15 hours
  3. customthe organic phase was separated
  4. extractionThe aqueous phase was extracted with hexane
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe inorganic substances were filtered off
  7. distillationthe organic solvent was distilled off under a reduced pressure
  8. distillationThe resultant oily residue was distilled under a pressure of 0.1 mmHg (116°-120° C.)

Sources & evidence

ORD record
ord-ce4e4e56cede482fabda5e453dc495f2
Source dataset
uspto-grants-1993_10
Patent number
US05254713

Reaction notes

Loading…