Potassium Iodide → HCID 12531860, compound

HRID 1704057Notes

Reaction equation

HRID 1704057 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C[O-].[Na+].[I-].[K+].Br[CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)[C:17]([O:19][CH3:20])=[O:18]>CO.C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:8])[CH:7]=1)[O:9][CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)=[CH:23][CH:22]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 115713,5-DichlorophenolHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531860HCID 12531860, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4.08 g of 3,5-dichlorophenol, 1.188 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 maintained at reflux overnight and then added to 100 ml of water. The product is then extracted with ether, and the ether is washed with 5% sodium hydroxide, water, brine, and dried (MgSO4). Evaporation of the solvent yields an oil which is chromatographed on 100 g of silica gel (benzene, 400 ml) to yield a yellow oil.

Workup

  1. temperatureThe mixture is maintained
  2. temperatureat reflux overnight
  3. extractionThe product is then extracted with ether
  4. washthe ether is washed with 5% sodium hydroxide, water, brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent
  7. customyields an oil which
  8. customis chromatographed on 100 g of silica gel (benzene, 400 ml)
  9. customto yield a yellow oil

Sources & evidence

ORD record
ord-85d3bd56a0454be1b8f66e783e746fa7
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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