2,4-Dichlorophenol → Phenol, 2,4-dichloro-, potassium salt

HRID 435412Notes

Reaction equation

HRID 435412 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[OH-].[K+:11].CC1C=C(F)C=CC=1[N+]([O-])=O>O>[CH:5]1[C:6]([Cl:8])=[CH:7][C:2]([Cl:1])=[C:3]([O-:9])[CH:4]=1.[K+:11]

Participants

5

Reactant 3

HCID 84492,4-DichlorophenolHCID 14797Potassium HydroxideHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 23666959Phenol, 2,4-dichloro-, potassium salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Potassium 2,4-dichlorophenate is prepared by dissolving 6.5 g. (0.04 mole) of 2,4-dichlorophenol and 2.6 g. (0.04 mole) of 85% potassium hydroxide in 30 ml. of methanol and removing the solvent under reduced pressure. The solid residue is dissolved in 60 ml. of sulfolane and 6.2 g. (0.04 mole) of 3-methyl-4-nitrofluorobenzene is added. The resulting solution is heated at 85° C. for 3 hours then at 150° C. for one hour, cooled, diluted with water and extracted with ether/benzene. The extract is dried and the solvent removed. The residue is dissolved in hot isopropanol and on cooling 8.2 g. (69%) of 2,4-dichloro-3'-methyl-4'-nitrodiphenyl ether (m.p. 72.5°-73.5° C.) separated and is isolated by filtration.

Workup

  1. dissolutionby dissolving 6.5 g
  2. customof methanol and removing the solvent under reduced pressure
  3. dissolutionThe solid residue is dissolved in 60 ml
  4. temperaturecooled
  5. extractionextracted with ether/benzene
  6. customThe extract is dried
  7. customthe solvent removed
  8. dissolutionThe residue is dissolved in hot isopropanol
  9. temperatureon cooling 8.2 g
  10. custom(69%) of 2,4-dichloro-3'-methyl-4'-nitrodiphenyl ether (m.p. 72.5°-73.5° C.) separated
  11. customis isolated by filtration

Sources & evidence

ORD record
ord-fb5a155e30384ca8bb4625956682a26f
Source dataset
uspto-grants-1983_08
Patent number
US04401461

Reaction notes

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