Potassium Iodide → HCID 12531856, compound

HRID 1863305Notes

Reaction equation

HRID 1863305 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.[I-].[K+].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.O>[Cl:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[O:11][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 4

HCID 4875Potassium IodideHCID 79333-ChlorophenolHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531856HCID 12531856, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1.19 g of sodium methoxide and 3.21 g of m-chlorophenol in 40 ml of methanol is added 50 mg of potassium iodide and 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The mixture is refluxed overnight and poured into 100 ml of water. The mixture is extracted with ether and the ether extracts washed with 5% NaOH, water, saturated NaCl solution and dried (MgSO4). The solvent is removed under vacuum to give an oil. Chromatography over silica gel (solvent-benzene) gives the product as a pale yellow oil.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. extractionThe mixture is extracted with ether
  3. washthe ether extracts washed with 5% NaOH, water, saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. customThe solvent is removed under vacuum
  6. customto give an oil

Sources & evidence

ORD record
ord-b2619b5e0a1c485fa0e221b606075ced
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

Loading…