Hydrogen Peroxide → HCID 13066702, compound

HRID 1163983Notes

Reaction equation

HRID 1163983 reaction equation
O=[O+][O-].[C:4]([O:7][C:8]1[C:13]([CH2:14]C=C)=[CH:12][CH:11]=[CH:10][C:9]=1[O:17][C:18]1[C:19]([CH3:24])=[CH:20][CH:21]=[CH:22][CH:23]=1)(=[O:6])C.OO.S([O-])(O)=O.[Na+]>C(O)(=O)C>[C:19]1([CH3:24])[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[O:17][C:9]1[C:8]2[O:7][C:4](=[O:6])[CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 24823OzoneHCID 13066658HCID 13066658, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13066702HCID 13066702, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ozone gas was introduced into a solution of o-tolyl 2-acetoxy-3-allylphenyl ether (5.64 g) in acetic acid (80 ml) at 15° C. with stirring for 45 minutes. 30% Hydrogen peroxide (4 ml) was added to the solution and allowed to stand overnight at room temperature. Aqueous sodium hydrogen sulfite was added to the solution, and the mixture was extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate and then evaporated. The oily residue (4.0 g) was dissolved in a mixture of sodium hydroxide and methanol. The solution was allowed to stand at room temperature for 30 minutes, and methanol was distilled off. The residue was washed with diethyl ether, acidified with dil. hydrochloric acid and then extracted with diethyl ether. The extract was dried over magnesium sulfate and evaporated. The oily residue (2.10 g) was dissolved in acetic anhydride (20 ml), heated on a water bath for 10 minutes and then evaporated. The crystalline residue was recrystallized from methanol to give colorless needles of 7-(o-tolyloxy)-2,3-dihydrobenzofuran-2-one (1.10 g). mp 110°-111° C.

Workup

  1. waitto stand overnight at room temperature
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. dissolutionThe oily residue (4.0 g) was dissolved in a mixture of sodium hydroxide and methanol
  7. waitto stand at room temperature for 30 minutes
  8. distillationmethanol was distilled off
  9. washThe residue was washed with diethyl ether
  10. extractionextracted with diethyl ether
  11. dry with materialThe extract was dried over magnesium sulfate
  12. customevaporated
  13. dissolutionThe oily residue (2.10 g) was dissolved in acetic anhydride (20 ml)
  14. temperatureheated on a water bath for 10 minutes
  15. customevaporated
  16. customThe crystalline residue was recrystallized from methanol

Sources & evidence

ORD record
ord-41b4a76137dd4449ba8ef63a2e7a5d9c
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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