Potassium Iodide → HCID 12531859, compound

HRID 1704055Notes

Reaction equation

HRID 1704055 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].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]=[CH:6][C:7]=1[Cl:8])[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 72583,4-DichlorophenolHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531859HCID 12531859, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4.08 g of 3,4-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 poured into 100 ml of water. The product is extracted with ether and the extracts are washed with 5% NaOH, water and 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 extracted with ether
  4. washthe extracts are washed with 5% NaOH, water and 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-01c70ad2becd4934956d536245d3ba48
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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