Water → 4-[(2-Chloro-2-propen-1-yl)oxy]benzonitrile

HRID 1493210Notes

Reaction equation

HRID 1493210 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]([CH2:19]Cl)=[CH2:18].O>CN(C)C=O>[Cl:16][C:17](=[CH2:18])[CH2:19][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 65652,3-DichloropropeneHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

Product 1

HCID 147741884-[(2-Chloro-2-propen-1-yl)oxy]benzonitrileYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.0 g of 4-cyanophenol and 11.6 g of potassium carbonate were suspended in 100 ml of dimethylformamide, and 9.4 g of 2,3-dichloropropene was added dropwise. The reaction solution was stirred at 80 oC for 3 hours, allowed to cool, and poured into 200 ml of water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried. Ethyl acetate was evaporated under reduced pressure. The resulting oily product was purified by column chromatography (silica gel; developing solvent hexane/ethyl acetate (9:1)) to give 15.2 g of the desired 4-(2-chloro-2-propeneoxy)benzonitrile as an oil.

Workup

  1. temperatureto cool
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. customdried
  5. customEthyl acetate was evaporated under reduced pressure
  6. customThe resulting oily product was purified by column chromatography (silica gel; developing solvent hexane/ethyl acetate (9:1))

Sources & evidence

ORD record
ord-1783545ae5444919aecfa6a6511db3e0
Source dataset
uspto-grants-1991_06
Patent number
US05021412

Reaction notes

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