Acetic Acid → 2-Methylfluorene

HRID 1089826

Reaktionsgleichung

Reaktionsgleichung von HRID 1089826
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=O.C(O)(=O)C.[H][H]>C(OCC)(=O)C.CCCCCC.[OH-].[OH-].[Pd+2]>[CH3:14][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:12][C:13]=2[CH:1]=1

Komponenten

7

Edukt 3

HCID 176Acetic AcidHCID 34804Fluorene-2-carboxaldehydeHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 150262-MethylfluoreneAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9942167Palladium hydroxideKatalysatorHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

A solution of 2-fluorenecarboxaldehyde (15 g, 77.1 mmol) in 250 mL of 10% solution of acetic acid in ethyl acetate was hydrogenated at 80 psi of hydrogen during 24 hours at room temperature over 20% palladium hydroxide on carbon (catalytic amount). The reaction was monitored by TLC (silica, 25% ethyl acetate in hexane). The catalyst was filtered off, evaporation of the solvents followed by recrystallization of the residual solid from ethanol:water 5:1 afforded 9.6 g (69.0%) of the product as colorless solid.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. customevaporation of the solvents
  3. customfollowed by recrystallization of the residual solid from ethanol:water 5:1

Quellen und Nachweise

ORD-Eintrag
ord-8f6e1c3af9924fbfa04f62eb84f9198e
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05079260

Verknüpfte Notizen

Wird geladen…