9-Formyl-2,7-fluorenedicarboxylic acid dibenzyl ester → 9-Formyl-9H-fluorene-2,7-dicarboxylic acid

HRID 1048820

Reaktionsgleichung

Reaktionsgleichung von HRID 1048820
C([O:8][C:9]([C:11]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][C:17]([C:24]([O:26]CC4C=CC=CC=4)=[O:25])=[CH:18][CH:19]=3)[CH:14]([CH:34]=[O:35])[C:13]=2[CH:12]=1)=[O:10])C1C=CC=CC=1.[H][H]>C1COCC1.[Pd]>[CH:34]([CH:14]1[C:15]2[CH:16]=[C:17]([C:24]([OH:26])=[O:25])[CH:18]=[CH:19][C:20]=2[C:21]2[C:13]1=[CH:12][C:11]([C:9]([OH:10])=[O:8])=[CH:23][CH:22]=2)=[O:35]

Komponenten

5

Edukt 2

HCID 866097799-Formyl-2,7-fluorenedicarboxylic acid dibenzyl esterHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 587760249-Formyl-9H-fluorene-2,7-dicarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a Parr hydrogenation bottle (Parr Instrument Company, Moline Ill.) was dissolved 9-formyl-2,7-fluorenedicarboxylic acid dibenzyl ester (3.0 g, 0.0061 mol) in THF anh. (350 mL). After careful addition of 20% Pd/C (wet with 50% water) 20% by weight (600 mg), the Parr bottle was evacuated/filled 3 times on a Parr apparatus to ensure hydrogen atmosphere. The suspension was shaken under 20-30 psi hydrogen gas for approximately 60 hours and then the remaining hydrogen was removed at reduced pressure. The suspension was filtered over a bed of celite, rinsed with additional THF and evaporated. 1H-NMR (d6-DMSO): δ (ppm) 9.0 (s, 1H, Ar); 8.5-8.1 (m, 6H, Ar).

Aufarbeitung

  1. additionthe Parr bottle was evacuated/filled 3 times on a Parr apparatus
  2. customthe remaining hydrogen was removed at reduced pressure
  3. filtrationThe suspension was filtered over a bed of celite
  4. washrinsed with additional THF
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d52af51c7b4d44f09a49cd67615d7a2b
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09381254B2

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