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

HRID 650915Notes

Reaction equation

HRID 650915 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-79430c54e25a4a7e9fc6f6fe2fcf2421
Source dataset
uspto-grants-2001_08
Patent number
US06277843B1

Reaction notes

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