Octadecyl 4-nitrobenzoate → Octadecyl 4-aminobenzoate

HRID 40423

Reaktionsgleichung

Reaktionsgleichung von HRID 40423
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:9])=[CH:6][CH:5]=1)([O-])=O>[Pt].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:9])=[CH:29][CH:30]=1

Komponenten

4

Edukt 1

HCID 11200948Octadecyl 4-nitrobenzoate

Produkt 1

HCID 19065294Octadecyl 4-aminobenzoateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under a nitrogen purge, 10% platinum on carbon (2.0 grams) was added to a mixture of octadecyl 4-nitrobenzoate (23 grams, 55 mmol) and ethyl acetate (230 milliliters) in a Parr vessel. The vessel was placed under hydrogen pressure (49 psi, 3.3×105 Pa) for sixteen hours. Added chloroform and filtered the reaction mixture through a layer of CELITE filter aid. The filtrate was concentrated under reduced pressure to light tan solid. The solid was recrystallized from ethanol to obtain 18 grams of octadecyl 4-aminobenzoate as a white solid.

Aufarbeitung

  1. customUnder a nitrogen purge
  2. customfor sixteen hours
  3. filtrationAdded chloroform and filtered the reaction mixture through a layer of CELITE
  4. filtrationfilter aid
  5. concentrationThe filtrate was concentrated under reduced pressure to light tan solid
  6. customThe solid was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-28a9bbf815274b20b6b146529d64edcb
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08529671B2

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