Aniline → Suberanilic Acid

HRID 418749

Reaktionsgleichung

Reaktionsgleichung von HRID 418749
[C:1]([OH:12])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[C:8]([OH:10])(=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12]

Komponenten

4

Edukt 2

HCID 6115Aniline2×HCID 10457Suberic acid2×

Produkt 1

HCID 9543537Suberanilic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Suberic acid (Compound 1, 174.2 g, 1.0 mole), aniline (Compound 2, 85.8-94.9 g), and toluene (0.1-0.2 L) are combined, heated to reflux and refluxed for a minimum of 60 hours. The reaction is quenched at reflux by adjusting the pH to ≧11 with 10% sodium hydroxide solution. The aqueous phase is separated. The organic layer is combined with toluene (0.11-0.13 L) and water (0.3-0.4 L), and the aqueous layer is separated. The aqueous layers from the extractions and toluene (0.11-0.13 L) are combined, settled, and then separated. The aqueous layer is extracted twice with toluene (0.2-0.3 L) at 60-70° C. The aqueous layer is adjusted at 20-30° C. to a pH of 5.8-6.2, using hydrochloric acid and 10% sodium hydroxide solution as needed. The batch is filtered, washed with chilled water (0.2-0.3 L) and then washed with chilled isopropanol. The wet cake is dried at a maximum of 65° C. under vacuum to yield suberanilic acid.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux
  3. temperaturerefluxed for a minimum of 60 hours
  4. customThe reaction is quenched
  5. temperatureat reflux
  6. customThe aqueous phase is separated
  7. customthe aqueous layer is separated
  8. extractionThe aqueous layers from the extractions and toluene (0.11-0.13 L)
  9. customseparated
  10. extractionThe aqueous layer is extracted twice with toluene (0.2-0.3 L) at 60-70° C
  11. customis adjusted at 20-30° C. to a pH of 5.8-6.2
  12. filtrationThe batch is filtered
  13. washwashed with chilled water (0.2-0.3 L)
  14. washwashed with chilled isopropanol
  15. customThe wet cake is dried at a maximum of 65° C. under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-307751a5df8a4086aa6bb3814be156d7
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093295B2

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