Hydrogen iodide → HCID 13066710, compound

HRID 1164046Notes

Reaction equation

HRID 1164046 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[F: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[F:17])[C:4]=2[O:20][C:19]1=[O:21]

Participants

5

Reactant 3

HCID 24841Hydrogen iodideHCID 20513491HCID 20513491, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13066710HCID 13066710, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Hydriodic acid (55-58%, 30 ml) was added portionwise to a solution of 2-[2-methoxy-3-(2-fluorophenoxy)phenyl]propionic acid (3.8 g) in acetic anhydride (15 ml) with stirring under ice-cooling, and the mixture was refluxed under heating for 15 minutes. After cooling, 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 then evaporated. The residue was purified by column chromatography (silica gel, benzene) and crystallization from ethanol to give 3-methyl-7-(2-fluorophenoxy)-2,3-dihydrobenzofuran-2-one (1.95 g). mp 70°-71.5° C.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 15 minutes
  4. temperatureAfter cooling
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with aqueous sodium hydrogen sulfite and water
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography (silica gel, benzene) and crystallization from ethanol

Sources & evidence

ORD record
ord-7e5bc8a8f83a472fbf536039fec6afcd
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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