Methanol → 2,7-Dimethylfluorene

HRID 1089840Notes

Reaction equation

HRID 1089840 reaction equation
[CH3:1][C:2]1[C:3](=O)[C:4]2[C:12](=[CH:13][CH:14]=1)[C:11]1[C:6](=[CH:7][C:8]([CH3:15])=[CH:9][CH:10]=1)[CH:5]=2.CO.C(OCC)(=O)C.[H][H]>[OH-].[Pd+2].[OH-].C(OCC)(=O)C.CCCCCC.C(O)(=O)C>[CH3:15][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[C:4](=[CH:3][C:2]([CH3:1])=[CH:14][CH:13]=3)[CH2:5][C:6]=2[CH:7]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 67719545HCID 67719545, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 1013472,7-DimethylfluoreneYield 89.5%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 2,7-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%, 0.5g) was hydrogenated in a shaker at 26 psi of hydrogen for 4 hr. The reaction was monitored by TLC (silica, 10% ethyl acetate/hexane). The catalyst was filtered out and the solvents were removed in vacuum. Treatment of the residue with methanol afforded 5.7 g (89.3%) of 2,7-dimethylfluorene.

Workup

  1. filtrationThe catalyst was filtered out
  2. customthe solvents were removed in vacuum

Sources & evidence

ORD record
ord-e0e4ca2bfae348a3a38398336ab1b897
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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