Water → HCID 14579590, compound

HRID 465480Notes

Reaction equation

HRID 465480 reaction equation
[OH2:1].O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[F:14][C:15]1[CH:27]=[C:26]([F:28])[C:25]2[C:24]3[C:19](=[CH:20][C:21]([F:31])=[CH:22][C:23]=3[O:29][CH3:30])[CH2:18][C:17]=2[CH:16]=1.O>C(O)(=O)C>[F:14][C:15]1[CH:27]=[C:26]([F:28])[C:25]2[C:24]3[C:19](=[CH:20][C:21]([F:31])=[CH:22][C:23]=3[O:29][CH3:30])[C:18](=[O:1])[C:17]=2[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 108005Sodium dichromate dihydrateHCID 15037292HCID 15037292, compound

Product 1

HCID 14579590HCID 14579590, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium dichromate dihydrate (2 eq, 0.26 mol, 7.9 g) was added to a solution 2,4,7-trifluoro-5-methoxy-9H-fluorene (3.3 g, 0.013 mol) in 100 mL of acetic acid and the mixture was refluxed for 5 h. The cooled reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extract was washed with saturated aqueous sodium bicarbonate and water, dried over MgSO4, and concentrated to leave 3 g of a yellow solid which was chromatographed on silica gel using 15% ethyl acetate in hexane to provide 2.0 g (57%) of the fluorenone: mp 164°-166° C.

Workup

  1. temperaturethe mixture was refluxed for 5 h
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with saturated aqueous sodium bicarbonate and water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5bdaaf92c8a148de80dc216573df552e
Source dataset
uspto-grants-1992_10
Patent number
US05153211

Reaction notes

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