Hydrogen Peroxide → HCID 19016870, compound

HRID 1197913Notes

Reaction equation

HRID 1197913 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][CH2:7]2)[CH3:2].OO.S(=O)(=O)(O)[OH:15]>C(O)=O>[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][C:6](=[O:15])[CH2:7]2)[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 18314920HCID 18314920, compound

Product 1

HCID 19016870HCID 19016870, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

33.9 g (235 mmol) of 4-ethylindene (a2) were slowly added dropwise to a mixture of 141 ml of formic acid (98-100% strength) and 33 ml (340 mmol) of H2O2 (35% strength), while cooling with ice (highly exothermic reaction). The mixture was then stirred at room temperature for a further 2.5 hours. The yellow-orange suspension formed was freed from excess formic acid under a water pump vacuum. 900 ml of 2N sulfuric acid were added to the yellow oil which remained. A total of 3 l of water were distilled over, while topping up with water, the product separating out in the receiver as a yellowish oil. The distillate was neutralized with saturated sodium carbonate solution and extracted with ether. The ether phase was dried over sodium sulfate and evaporated. 22.4 g (59%) of the compound a3 were obtained as a white solid.

Workup

  1. temperaturewhile cooling with ice (
  2. customhighly exothermic reaction)
  3. customThe yellow-orange suspension formed
  4. distillationA total of 3 l of water were distilled over,
  5. customthe product separating out in the receiver as a yellowish oil
  6. extractionextracted with ether
  7. dry with materialThe ether phase was dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-cf1ae448ef8f427abafd5fa8cb984bec
Source dataset
uspto-grants-1994_01
Patent number
US05278264

Reaction notes

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