Hydrogen iodide → HCID 20513439, compound

HRID 1164099Notes

Reaction equation

HRID 1164099 reaction equation
C([C:3]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[C:14]=1OC)([CH2:9][CH2:10][CH2:11][CH3:12])[C:4]([O:6]CC)=[O:5])#N.I.S([O-])(O)=O.[Na+]>C(O)(=O)C>[CH2:9]([CH:3]1[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[C:14]=2[O:5][C:4]1=[O:6])[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 24841Hydrogen iodideHCID 20513463HCID 20513463, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 20513439HCID 20513439, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 2-cyano-2-[2-methoxy-3-(o-tolyloxy)phenyl]-n-hexanoate (6.5 g), hydriodic acid (58%, 10 ml) and glacial acetic acid (20 ml) was refluxed under heating for 47 hours. After cooling, the reaction mixture was poured into dil. aqueous sodium hydrogen sulfite and extracted with diethyl ether. The extract was washed with water, dil. aqueous sodium hydrogen sulfite and water in turn, dried and evaporated under reduced pressure. To the oily residue was added acetic anhydride (10 ml), and the mixture was refluxed under heating for 10 minutes and evaporated under reduced pressure. Water and ethanol were added to the residue, and the mixture was concentrated under reduced pressure. The oily residue was purified by column chromatography (silica gel 80 g, benzene) to give 3-(n-butyl) 7-(o-tolyloxy)-2,3-dihydrobenzofuran-2-one (2.8 g).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 47 hours
  3. temperatureAfter cooling
  4. extractionextracted with diethyl ether
  5. washThe extract was washed with water, dil. aqueous sodium hydrogen sulfite and water in turn
  6. customdried
  7. customevaporated under reduced pressure
  8. additionTo the oily residue was added acetic anhydride (10 ml)
  9. temperaturethe mixture was refluxed
  10. temperatureunder heating for 10 minutes
  11. customevaporated under reduced pressure
  12. additionWater and ethanol were added to the residue
  13. concentrationthe mixture was concentrated under reduced pressure
  14. customThe oily residue was purified by column chromatography (silica gel 80 g, benzene)

Sources & evidence

ORD record
ord-049659a374554d69bcb1c0f6615cae2e
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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