Hydrogen Peroxide → 5-(4-(Acetyloxy)phenyl)-2-benzofurancarboxylic acid

HRID 2057973Notes

Reaction equation

HRID 2057973 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].OO.C([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[CH:21][C:22]3[O:26][C:25]([C:27]([OH:29])=[O:28])=[CH:24][C:23]=3[CH:30]=2)=[CH:15][CH:14]=1)(=O)C>C(O)(=O)C>[C:3]([O:5][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[CH:21][C:22]3[O:26][C:25]([C:27]([OH:29])=[O:28])=[CH:24][C:23]=3[CH:30]=2)=[CH:15][CH:14]=1)(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 203296455-(4-Acetylphenyl)-2-benzofurancarboxylic acid

Product 1

HCID 203296395-(4-(Acetyloxy)phenyl)-2-benzofurancarboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2 ml of trifluoroacetic acid and 92 ml of 30% hydrogen peroxide solution were added to a mixture of 13 g of 10 in 300 ml of acetic acid. The mixture was heated at 70°-75° C. for 10 hours, then was cooled in a refrigerator. The solid that formed was collected and dried. The acetic acid solution was poured into 3.6 liters of ice water. The solid that formed was collected and dried (P2O5). The two solids were combined and dissolved in 150 ml of tetrahydrofuran. The solution was filtered, concentrated to 20 ml and chilled. The solid that formed was collected, dried under reduced pressure, and recrystallized from tetrahydrofuran to give 11, mp: 251°-254° C.

Workup

  1. temperatureThe mixture was heated at 70°-75° C. for 10 hours
  2. temperaturewas cooled in a refrigerator
  3. customThe solid that formed
  4. customwas collected
  5. customdried
  6. additionThe acetic acid solution was poured into 3.6 liters of ice water
  7. customThe solid that formed
  8. customwas collected
  9. dry with materialdried (P2O5)
  10. dissolutiondissolved in 150 ml of tetrahydrofuran
  11. filtrationThe solution was filtered
  12. concentrationconcentrated to 20 ml
  13. temperaturechilled
  14. customThe solid that formed
  15. customwas collected
  16. customdried under reduced pressure
  17. customrecrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-e2c182f0864b45cda44083cfca899a96
Source dataset
uspto-grants-1980_07
Patent number
US04213998

Reaction notes

Loading…