Hydrogen iodide → HCID 13066721, compound

HRID 1164021Notes

Reaction equation

HRID 1164021 reaction equation
CO[C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:17][CH2:18][C:19]([OH:21])=[O:20].I>C(OC(=O)C)(=O)C>[C:11]1([CH3:16])[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[O:9][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[O:21][C:19](=[O:20])[CH2:18][CH2:17]2

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 13066685HCID 13066685, compound

Product 1

HCID 13066721HCID 13066721, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 3-[2-methoxy-3-(o-tolyloxy)phenyl]propionic acid (15 g) in acetic anhydride (40 ml) was added dropwise to 48% hydriodic acid (80 ml) with stirring under ice-cooling in 5 minutes, and after removing methyl iodide, the mixture was refluxed under heating for 20 minutes. After cooling, the reaction mixture was evaporated, and water was added to the residue and extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate and evaporated. The residue was added to a mixture of benzene (50 ml) and acetic anhydride (30 ml) and refluxed under heating for an hour. After cooling, the mixture was evaporated, and the residue was dissolved in diethyl ether, washed with water, aqueous sodium hydroxide and water successively, dried and then evaporated. The oily residue (13.8 g) was pulverized with n-hexane to give 8-(o-tolyloxy)chroman-2-one (11.4 g). This substance was purified by recrystallization from a mixture of ethanol and n-hexane. mp 80°-82° C.

Workup

  1. temperaturecooling in 5 minutes
  2. customafter removing methyl iodide
  3. temperaturethe mixture was refluxed
  4. temperatureunder heating for 20 minutes
  5. temperatureAfter cooling
  6. customthe reaction mixture was evaporated
  7. additionwater was added to the residue
  8. extractionextracted with diethyl ether
  9. washThe extract was washed with water
  10. dry with materialdried over magnesium sulfate
  11. customevaporated
  12. additionThe residue was added to a mixture of benzene (50 ml) and acetic anhydride (30 ml)
  13. temperaturerefluxed
  14. temperatureunder heating for an hour
  15. temperatureAfter cooling
  16. customthe mixture was evaporated
  17. dissolutionthe residue was dissolved in diethyl ether
  18. washwashed with water, aqueous sodium hydroxide and water successively
  19. customdried
  20. customevaporated

Sources & evidence

ORD record
ord-2287d7b8a083435498efbdd3c7af873a
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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