Hydrogen Peroxide → 9h-fluoren-2-yl acetate

HRID 2416351Notes

Reaction equation

HRID 2416351 reaction equation
S(=O)(=O)(O)O.C([C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][C:11]=2[CH:10]=1)(=O)C.[C:22]([O:25]C(=O)C)(=[O:24])[CH3:23].OO>O.C(O)=O>[C:22]([O:25][C:9]1[CH:21]=[CH:20][C:19]2[C:14]3[C:13](=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][C:11]=2[CH:10]=1)(=[O:24])[CH3:23]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 699082-Acetylfluorene

Product 1

HCID 2470609h-fluoren-2-yl acetateYield 83.9%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

Sulfuric acid (40 mL) was added to a mixture of 2-acetylfluorene (165 g), formic acid (320 g), acetic anhydride (120 g) and dicholoromethane (1 L), and then aqueous hydrogen peroxide (120 mL) was dropwise added thereto. The solution was stirred for 30 minutes at a room temperature, and it was heated up to 40° C. and further stirred for 5 hours. Water (1 L) was added to the reaction mixture, and the dichloromethane layer was separated. The dichloromethane layer was washed in order with a saturated sodium carbonate aqueous solution, a sodium hydrogensulfite aqueous solution and water, and then it was dried on anhydrous magnesium sulfate and concentrated to obtain a solid matter. This was recrystallized from a mixed solvent of heptane-ethyl acetate (1:1) to obtain 2-acetoxyfluorene (149 g) of colorless needle crystal. The melting point was 130 C.

Workup

  1. temperatureit was heated up to 40° C.
  2. stirringfurther stirred for 5 hours
  3. customthe dichloromethane layer was separated
  4. washThe dichloromethane layer was washed in order with a saturated sodium carbonate aqueous solution
  5. dry with materiala sodium hydrogensulfite aqueous solution and water, and then it was dried on anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto obtain a solid matter
  8. customThis was recrystallized from a mixed solvent of heptane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-0ea5664139024967b164e558b7400518
Source dataset
uspto-grants-2004_11
Patent number
US06824709B2

Reaction notes

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