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

HRID 1594557Notes

Reaction equation

HRID 1594557 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-f1af2d16f3be4d8388df31de47125b1c
Source dataset
uspto-grants-2001_09
Patent number
US06284753B1

Reaction notes

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