Hydrogen iodide → HCID 13139430, compound

HRID 1164029Notes

Reaction equation

HRID 1164029 reaction equation
I.CO[C:4]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:18]([CH3:22])[C:19]([OH:21])=[O:20].S([O-])(O)=O.[Na+]>C(OC(=O)C)(=O)C>[CH3:22][CH:18]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[O:20][C:19]1=[O:21]

Participants

5

Reactant 3

HCID 24841Hydrogen iodideHCID 20513459HCID 20513459, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13139430HCID 13139430, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Hydriodic acid (55-58%, 20 ml) was added to a solution of 2-[2-methoxy-3-(2-chlorophenoxy)phenyl]propionic acid (2.7 g) in acetic anhydride (10 ml) under ice-cooling. The mixture was refluxed under heating for 30 minutes. The reaction mixture was poured into aqueous solution of sodium hydrogen sulfite and extracted with diethyl ether. The extract was washed with aqueous sodium hydrogen sulfite and water, dried and evaporated. To the oily residue was added acetic anhydride (10 ml), and the mixture was refluxed under heating for 30 minutes. After cooling, the mixture was evaporated, and the oily residue was dissolved in diethyl ether. The solution was washed with saturated aqueous sodium bicarbonate and water, dried and then evaporated. The residue was subjected to column chromatography on silica gel (40 g) and eluted with benzene, and the eluate was evaporated. The oily residue was crystallized with n-hexane to give 3-methyl-7-(2-chlorophenoxy)-2,3-dihydrobenzofuran-2-one (1.15 g). mp 92°-95° C.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was refluxed
  3. temperatureunder heating for 30 minutes
  4. extractionextracted with diethyl ether
  5. washThe extract was washed with aqueous sodium hydrogen sulfite and water
  6. customdried
  7. customevaporated
  8. additionTo the oily residue was added acetic anhydride (10 ml)
  9. temperaturethe mixture was refluxed
  10. temperatureunder heating for 30 minutes
  11. temperatureAfter cooling
  12. customthe mixture was evaporated
  13. dissolutionthe oily residue was dissolved in diethyl ether
  14. washThe solution was washed with saturated aqueous sodium bicarbonate and water
  15. customdried
  16. customevaporated
  17. washeluted with benzene
  18. customthe eluate was evaporated
  19. customThe oily residue was crystallized with n-hexane

Sources & evidence

ORD record
ord-5389de70440a49218d1d8f946ca0ba97
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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