4-Chlorophenol → 1-(4-Chlorophenoxy)-2-chloro-2-propene

HRID 1166324Notes

Reaction equation

HRID 1166324 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:15][C:16]([CH2:18]Cl)=[CH2:17]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][C:16]([Cl:15])=[CH2:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 65652,3-DichloropropeneHCID 11430Potassium Carbonate

Product 1

HCID 122548641-(4-Chlorophenoxy)-2-chloro-2-propeneYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 4-chlorophenol (6.1 g, 47.4 mmol) and potassium carbonate (13.1 g, 94.7 mmol) in acetone (200 mL), 2,3-dichloropropene (6.6 mL, 71 mmol) was added. After heating to reflux the reaction mixture for 48 hours, the reaction mixture was cooled and filtered. The residue was washed with more acetone and the combined filtrates were concentrated in vacuo. The crude pale brown liquid (11.5 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 85/15) to give 1-(4-chlorophenoxy)-2-chloro-2-propene (8.9 g, 98%) as a white liquid: Anal. Calc'd. for C9H8OCl2: C, 53.23, H, 3.97. Found: C, 53.09, H, 3.95.

Workup

  1. additionwas added
  2. temperatureAfter heating
  3. temperatureto reflux the reaction mixture for 48 hours
  4. temperaturethe reaction mixture was cooled
  5. filtrationfiltered
  6. washThe residue was washed with more acetone
  7. concentrationthe combined filtrates were concentrated in vacuo
  8. customThe crude pale brown liquid (11.5 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 85/15)

Sources & evidence

ORD record
ord-42ee6d520ce5418f99fe0345d513e558
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

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