Potassium Iodide → Methyl (m-[m-phenoxyphenoxy]phenoxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

HRID 1863300Notes

Reaction equation

HRID 1863300 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][CH:21]=1)[O:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[I-].[K+].Br[CH:28]([C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)=[CH:35][CH:34]=1)[C:29]([O:31][CH3:32])=[O:30]>CO.C1C=CC=CC=1.O>[O:1]([C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][CH:21]=1)[O:11][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][CH:28]([C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]2[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=2)=[CH:35][CH:34]=1)[C:29]([O:31][CH3:32])=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 84251Phenol, 3-(3-phenoxyphenoxy)-HCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 86736645Methyl (m-[m-phenoxyphenoxy]phenoxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6.96 g of m-(m-phenoxyphenoxy)phenol, 1.19 g of sodium methoxide and 50 mg of potassium iodide 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. The mixture is refluxed for 20 hours, poured into ice and water and extracted with chloroform. The chloroform extracts are washed with 10% potassium carbonate and with water. The extract is dried over magnesium sulfate and concentrated under vacuum to give an oil. Filtration once through silica gel (chloroform solvent) and again through silica gel with benzene as solvent gives the product as an oil.

Workup

  1. temperatureThe mixture is refluxed for 20 hours
  2. extractionextracted with chloroform
  3. washThe chloroform extracts are washed with 10% potassium carbonate and with water
  4. dry with materialThe extract is dried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customto give an oil
  7. filtrationFiltration once through silica gel (chloroform solvent)

Sources & evidence

ORD record
ord-bda675eb7dbd4415a813c129aea4875b
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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