Hydrogen Peroxide → 2,7-Diacetyloxyfluorene

HRID 2416361Notes

Reaction equation

HRID 2416361 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].C(C1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][C:17]([O:24][C:25](=[O:27])[CH3:26])=[CH:18][CH:19]=3)[CH2:14][C:13]=2C=1)(=O)C.S(=O)(=O)(O)O.OO.C(=O)([O-])O.[Na+]>O.ClCCl.C(O)=O>[C:5]([O:4][C:1]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][C:17]([O:24][C:25](=[O:27])[CH3:26])=[CH:18][CH:19]=3)[CH2:14][C:13]=2[CH:2]=1)(=[O:7])[CH3:6]

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 226302682-Acetyl-7-acetoxyfluorene

Product 1

HCID 122960592,7-DiacetyloxyfluoreneYield 47.2%

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (26.2 g) and 88% formic acid (68 g) were added in order to a mixture of 2-acetyl-7-acetoxyfluorene (45 g) and dichloromethane (450 mL). 36M-sulfuric acid (9 mL) was slowly added thereto at 9° C., and then a 34% hydrogen peroxide aqueous solution (25.9 g) was added to obtain a ocherous reaction mixture. This reaction mixture was refluxed for 9 hours by heating, and then it was cooled down to a room temperature and poured into water. The mixture was neutralized with saturated sodium hydrogencarbonate, and then the organic layer was sufficiently washed with 10% sodium hydrogensulfite to remove unreacted peroxide. The separated organic layer was concentrated under reduced pressure, and the resulting residue was purified by means of column chromatography (silica gel, eluting solvent: ethyl acetate) to obtain 2,7-diacetyloxyfluorene (22.5 g) of colorless crystal. Melting point: 167.6-168.3° C.

Workup

  1. customto obtain a ocherous reaction mixture
  2. temperatureThis reaction mixture was refluxed for 9 hours
  3. temperatureby heating
  4. washthe organic layer was sufficiently washed with 10% sodium hydrogensulfite
  5. customto remove unreacted peroxide
  6. concentrationThe separated organic layer was concentrated under reduced pressure
  7. customthe resulting residue was purified by means of column chromatography (silica gel, eluting solvent: ethyl acetate)

Sources & evidence

ORD record
ord-9415613b1e834ff8a41473b6e87e236f
Source dataset
uspto-grants-2004_11
Patent number
US06824709B2

Reaction notes

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