Hydrochloric Acid → HCID 12531852, compound

HRID 1863302Notes

Reaction equation

HRID 1863302 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].[OH-].[K+].Cl>CO.C1C=CC=CC=1.O.C(=O)(O)[O-].[Na+].C(O)C>[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

12

Reactant 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 97324-FluorophenolHCID 14797Potassium HydroxideHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531852HCID 12531852, compound

Reagents, catalysts & solvents 5

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 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 give 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. customto give a tan oil
  9. dissolutionThe oil is dissolved in 60 ml
  10. temperatureThe mixture is refluxed for 3.5 hours
  11. additionpoured onto ice
  12. extractionThe mixture is extracted with chloroform
  13. washthe extracts washed with water
  14. dry with materialdried over magnesium sulfate
  15. concentrationConcentration in vacuo
  16. customgives an oil
  17. extractionthe mixture extracted with chloroform
  18. extractionextracted with ether
  19. dry with materialthe extracts dried (MgSO4)
  20. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-abd2f09d140e452b891cedae2e8de159
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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