Hydrogen iodide → 7-(2-Chlorophenylthio)-2,3-dihydrobenzofuran-2-one

HRID 1164083Notes

Reaction equation

HRID 1164083 reaction equation
I.CO[C:4]1[C:9]([S: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[CH2:18][C:19]([OH:21])=[O:20].S([O-])(O)=O.[Na+]>C(OC(=O)C)(=O)C>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[S:10][C:9]1[C:4]2[O:21][C:19](=[O:20])[CH2:18][C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24841Hydrogen iodideHCID 20513473HCID 20513473, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 130667157-(2-Chlorophenylthio)-2,3-dihydrobenzofuran-2-oneYield 87.7%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Hydriodic acid (58%, 10 ml) was added dropwise to a solution of 2-[2-methoxy-3-(2-chlorophenylthio)phenyl]acetic acid (1.4 g) in acetic anhydride (5 ml), and the mixture was refluxed under heating for 15 minutes. After cooling, the reaction mixture was poured into an aqueous solution of sodium hydrogen sulfite. The mixture was extracted with diethyl ether, and the extract was washed with aqueous sodium hydrogen sulfite and water in turn, dried and then evaporated under reduced pressure. To the residue was added acetic anhydride (10 ml), and the mixture was refluxed under heating for 10 minutes, and then evaporated under reduced pressure to give crystalline 7-(2-chlorophenylthio)-2,3-dihydrobenzofuran-2-one (1.1 g). This product was recrystallized from ethanol to give the pure product (0.8 g), mp. 145°-146° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 15 minutes
  3. temperatureAfter cooling
  4. extractionThe mixture was extracted with diethyl ether
  5. washthe extract was washed with aqueous sodium hydrogen sulfite and water in turn
  6. customdried
  7. customevaporated under reduced pressure
  8. additionTo the residue was added acetic anhydride (10 ml)
  9. temperaturethe mixture was refluxed
  10. temperatureunder heating for 10 minutes
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-07ede28a5f314c48860a913d5d03ea85
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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