Methanol → 4,5-Dimethyl-9H-fluorene

HRID 1089844Notes

Reaction equation

HRID 1089844 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5](=O)[C:6]2[C:14]=1[C:13]1[C:8](=[CH:9][CH:10]=[CH:11][C:12]=1[CH3:15])[CH:7]=2.CO.C(OCC)(=O)C.[H][H]>[OH-].[Pd+2].[OH-].C(OCC)(=O)C.CCCCCC.C(O)(=O)C>[CH3:15][C:12]1[C:13]2[C:14]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[CH3:1])[CH2:7][C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 70233539HCID 70233539, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 143895334,5-Dimethyl-9H-fluoreneYield 91.2%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 4,5-dimethylfluorenone (7.0 g, 32.8 mmol), methanol (100 mL), ethyl acetate (50 mL), acetic acid (20 mL) and palladium hydroxide (20% on carbon, water content 44.43%, 1.0 g) was hydrogenated in a shaker at 35-40psi of hydrogen for 3.5 hr. The reaction was monitored by TLC (silica, 10% ethyl acetate/hexane). The catalyst was filtered off and the solvent was removed in vacuum, the residue was diluted with water (150 mL). The product was extracted with ethyl acetate (3×50 mL) and dried over magnesium sulfate. Evaporation of the solvent afforded 5.8 g (91.2%) of 4,5-dimethylfluorene.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed in vacuum
  3. additionthe residue was diluted with water (150 mL)
  4. extractionThe product was extracted with ethyl acetate (3×50 mL)
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-2603cfafa9d6421ea7bd41e0fca266bf
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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