Potassium Iodide → HCID 12531852, compound

HRID 1704043Notes

Reaction equation

HRID 1704043 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C[O-].[Na+].[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]C)=[O:17]>CO.C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:15]([C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[CH:24][CH:25]=2)[C:16]([OH:18])=[O:17])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 97324-FluorophenolHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531852HCID 12531852, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2.80 g of p-fluorophenol and 1.19 g of sodium methoxide 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 for 20 hours and the solvent removed under vacuum. 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). The solvent is removed under vacuum to given a tan oil. The oil is dissolved in 60 ml. of ethanol and 6 ml of water and 5 g of potassium hydroxide is added. The mixture is refluxed for 3.5 hours, acidified with concentrated hydrochloric acid, diluted with water and poured onto ice. The mixture is extracted with chloroform and the extracts washed with water and dried over magnesium sulfate. Concentration in vacuo gives an oil. The oil is dissolved in aqueous sodium bicarbonate and the mixture extracted with chloroform. The aqueous layer is acidified with concentrated hydrochloric acid, extracted with ether and the extracts dried (MgSO4). Removal of the solvent in vacuo gives the product as a tan oil. A small sample is crystallized, mp 106°-111° C.

Workup

  1. temperatureThe mixture is refluxed for 20 hours
  2. customthe solvent removed under vacuum
  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. customThe solvent is removed under vacuum
  8. dissolutionThe oil is dissolved in 60 ml
  9. additionof ethanol and 6 ml of water and 5 g of potassium hydroxide is added
  10. temperatureThe mixture is refluxed for 3.5 hours
  11. additiondiluted with water
  12. additionpoured onto ice
  13. extractionThe mixture is extracted with chloroform
  14. washthe extracts washed with water
  15. dry with materialdried over magnesium sulfate
  16. concentrationConcentration in vacuo
  17. customgives an oil
  18. extractionthe mixture extracted with chloroform
  19. extractionextracted with ether
  20. dry with materialthe extracts dried (MgSO4)
  21. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-72c968c7610c424e8f87e70015039165
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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