Ethyl Acetate → 4-Methylfluorene

HRID 1089822Notes

Reaction equation

HRID 1089822 reaction equation
O[CH:2]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:15]O)[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.CCOC(C)=O.[H][H]>[Pd].CC(O)=O>[CH3:15][C:10]1[C:9]2[C:8]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:2][C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2720524-(hydroxymethyl)-9h-fluoren-9-olHCID 178418361HCID 178418361, compound

Product 1

HCID 152564-MethylfluoreneYield 77.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 9-hydroxyfluoren-4-methanol (2.6 g, 12.2 mmol) in 1.1 EtOAc:AcOH was charged with catalytic amount of 10% palladium on charcoal. The mixture was treated with hydrogen under 1600 psi, at room temperature for three days. The catalyst was removed and the solvent was evaporated under reduced pressure. Recrystalyzation from MeOH afforded 1.7 g (77.0%) of the product as a light yellow solid.

Workup

  1. customThe catalyst was removed
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b24e7e79fc1b4f088fdc4c3c513258a6
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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