Acetic Acid → 2-Aminobenzhydrol

HRID 1377696

Reaktionsgleichung

Reaktionsgleichung von HRID 1377696
C(O)(=O)C.[BH4-].[Na+].[H][H].[NH2:9][C:10]1[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].C(=O)(O)[O-].[Na+]>C1COCC1.O.CCCCCC.CCOC(C)=O>[NH2:9][C:10]1[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=1[CH:12]([OH:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

10

Edukt 5

HCID 176Acetic AcidHCID 760802-AminobenzophenoneHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 2708102-Aminobenzhydrol

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Acetic acid (2.28 mL, 2.4 g, 40.4 mmol) was added slowly to sodium borohydride (0.76 g, 20.2 mmol) in THF (20 mL) stirred in an ice bath. The mixture was stirred in the cold until hydrogen evolution had ceased. 2-Aminobenzophenone (2.0 g, 10.1 mmol) was added as the solid. The mixtuire was stirred under nitrogen at ambient temperature for 20 hours, after which time, TLC assay (silica gel, 1:9 EtOAc:hexane) indicated reaction was complete. The reaction mixture was treated with water (40 mL), then neutralized with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layers were combined, dired over sodium sulfate, filtered, and evaporated to dryness in vacuo to give 2-aminobenzhydrol.

Aufarbeitung

  1. stirringThe mixtuire was stirred under nitrogen at ambient temperature for 20 hours
  2. customreaction
  3. extractionextracted with ethyl acetate
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1b677fc41a5343fbbd79c4676be40793
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05665719

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