4-Hydroxy-9-fluorenone → 9H-fluoren-4-ol

HRID 1533452Notes

Reaction equation

HRID 1533452 reaction equation
[OH:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H][H]>CCOC(C)=O.CCO.[Pd]>[OH:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 161394-Hydroxy-9-fluorenoneHCID 178418361HCID 178418361, compound

Product 1

HCID 1826409H-fluoren-4-ol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A partial solution of 196.2 mg (1 mmol) of 4-hydroxy-fluoren-9-one in 2 mL EtOAc and 3 mL EtOH with 40 mg 10% Pd/C was stirred under a balloon of hydrogen for 27.5 hours. The catalyst was removed by filtration through celite, washed well with EtOAc, and the filtrate evaporated. The residue was purified by plate layer chromatography with CH2Cl2-EtOAc(50:1) to give 102.7 mg of the title substance.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. washwashed well with EtOAc
  3. customthe filtrate evaporated
  4. customThe residue was purified by plate layer chromatography with CH2Cl2-EtOAc(50:1)
  5. customto give 102.7 mg of the title substance

Sources & evidence

ORD record
ord-ada04b5c77524307b1ff9ef5060b8c5f
Source dataset
uspto-grants-2001_03
Patent number
US06207823B1

Reaction notes

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