Hydrochloric Acid → HCID 58776026, Verbindung

HRID 1402630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1402630
[Al+3].[Cl-].[Cl-].[Cl-].[CH:5]1[C:17]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[C:8]([C:18]([OH:20])=[O:19])=[CH:7][CH:6]=1.[C:21]1(=[O:27])[O:26][C:24](=[O:25])[CH2:23][CH2:22]1.Cl>ClCCCl>[C:24]([CH2:23][CH2:22][C:21]([C:13]1[CH:14]=[C:15]2[C:10]([C:9]3[C:8]([C:18]([OH:20])=[O:19])=[CH:7][CH:6]=[CH:5][C:17]=3[CH2:16]2)=[CH:11][CH:12]=1)=[O:27])([OH:26])=[O:25]

Komponenten

6

Edukt 4

HCID 313Hydrochloric Acid2×HCID 7922Succinic anhydrideHCID 814029H-fluorene-4-carboxylic acidHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 58776026HCID 58776026, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a dry argon-purged round bottom flask anhydrous AlCl3 (26.9 g, 0.202 mol) was suspended in anhydrous 1,2-dichloroethane (60 mL). 4-Fluorenecarboxylic acid (10.0 g, 0.048 mol) was added to the suspension. The reaction flask was placed in a room temperature bath and succinic anhydride (5.72 g, 0.057 mol) was carefully added. The reaction was stirred for five hours and then cooled to 0° C. The reaction was very carefully quenched by the slow portion-wise addition of 3 M HCl (Caution! The reaction can react violently when HCl is added too rapidly.) The final well mixed suspension was acidic and not reactive to additional HCl solution. The organic solvent was removed at reduced pressure and the product was filtered and washed well with water. The crude product was dissolved in warm NaOH solution (approximately ≦1M NaOH), filtered and precipitated with the addition of concentrated HCl. The product was filtered washed with water and then dried at reduced pressure in the presence of P2O5. The product was a pale yellow solid (14.3 g, 97%). 1H-NMR (d6-DMSO): δ (ppm) 8.4 (d, 1H, Ar); 8.2 (s, 1H, Ar); 8.0 (d, 1H, Ar); 7.8 (m, 2H, Ar); 7.5 (t, 1H, Ar); 4.1 (s, 2H, CH2); 2.6 (t, 2H, CH2) 2.5 (under DMSO, CH2).

Aufarbeitung

  1. customwas placed in a room temperature
  2. customThe reaction was very carefully quenched by the slow portion-wise addition of 3 M HCl (Caution
  3. customThe reaction
  4. additionis added too rapidly
  5. addition) The final well mixed suspension
  6. customThe organic solvent was removed at reduced pressure
  7. filtrationthe product was filtered
  8. washwashed well with water
  9. dissolutionThe crude product was dissolved in warm NaOH solution (approximately ≦1M NaOH),
  10. filtrationfiltered
  11. customprecipitated with the addition of concentrated HCl
  12. filtrationThe product was filtered
  13. washwashed with water
  14. dry with materialdried at reduced pressure in the presence of P2O5

Quellen und Nachweise

ORD-Eintrag
ord-129216cf62aa4fa7a5800ba8eec5e73f
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08911718B2

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