3,4,5-Trichlorophenol → HCID 12531851, compound

HRID 1863303Notes

Reaction equation

HRID 1863303 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].C[O-].[Na+].Br[CH:15]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]>CO.C1C=CC=CC=1.[I-].[K+].C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8])[O:10][CH:15]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

8

Reactant 3

HCID 118593,4,5-TrichlorophenolHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531851HCID 12531851, compound

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 4875Potassium IodideSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 4.93 g of 3,4,5-trichlorophenol and 1.19 g of sodium methoxide in 40 ml of methanol is added 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene and 50 mg of potassium iodide. The mixture is refluxed for 20 hours and the solvent removed in vacuo. To the residue is added water and the mixture is extracted with ether. The ether extracts are washed with 10% potassium carbonate and with water and dried (MgSO4). Evaporation of the solvent under vacuum gives a tan oil. The oil is dissolved in chloroform and filtered through a column of silica gel. Removal of the solvent from the second 200 ml cut gives the product as a tan oil.

Workup

  1. temperatureThe mixture is refluxed for 20 hours
  2. customthe solvent removed in vacuo
  3. additionTo the residue is added water
  4. extractionthe mixture is extracted with ether
  5. washThe ether extracts are washed with 10% potassium carbonate and with water
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent under vacuum
  8. customgives a tan oil
  9. filtrationfiltered through a column of silica gel
  10. customRemoval of the solvent from the second 200 ml

Sources & evidence

ORD record
ord-61a057739ad14201a40aa486ccf675ea
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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