Potassium Iodide → 2-Allyl-3,4-dichlorophenol

HRID 34966

Reaction equation

HRID 34966 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:10](Br)[CH:11]=[CH2:12].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(C(C)=O)C>[CH2:12]([C:3]1[C:2]([Cl:1])=[C:7]([Cl:8])[CH:6]=[CH:5][C:4]=1[OH:9])[CH:11]=[CH2:10]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 72583,4-DichlorophenolHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 142330452-Allyl-3,4-dichlorophenol

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
200 °C

Procedure

A solution of 100 g. of 3,4-dichlorophenol, 50 ml. of allyl bromide, 84 g. of potassium carbonate, and 1.0 g. of potassium iodide in 500 ml. of methyl ethyl ketone was allowed to reflux overnight. The solution was then cooled, filtered, and evaporated to dryness. The residue was then heated at 200° C. for approximately four hours. NMR analysis indicated that the 113.6 g. of remaining material was primarily the desired 2-allyl-3,4-dichlorophenol.

Workup

  1. temperatureto reflux overnight
  2. temperatureThe solution was then cooled
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-99355c9dac3a4ade8fb9d00ba4a791bd
Source dataset
uspto-grants-1988_08
Patent number
US04764521

Linked notes

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