Ethyl Acetate → Tetradecyl 4-aminobenzoate

HRID 40421

Reaktionsgleichung

Reaktionsgleichung von HRID 40421
[N+:1]([C:4]1[CH:26]=[CH:25][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][CH3:24])=[O:9])=[CH:6][CH:5]=1)([O-])=O.C(OCC)(=O)C>[Pt].ClCCl>[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][CH3:24])=[O:9])=[CH:25][CH:26]=1

Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 591245Tetradecyl 4-nitrobenzoate

Produkt 1

HCID 66970570Tetradecyl 4-aminobenzoateAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under a nitrogen purge, 10% platinum on carbon (2.5 grams) was added to a mixture of tetradecyl 4-nitrobenzoate (25 grams, 69 mmol) and ethyl acetate (250 milliliters) in a Parr vessel. The vessel was placed under hydrogen pressure (49 psi, 3.3×105 Pa) for sixteen hours. Dichloromethane was added and the reaction mixture was filtered through a layer of CELITE filter aid. The filtrate was concentrated under reduced pressure to a tan solid. The solid was recrystallized from ethanol to obtain 15 grams of tetradecyl 4-aminobenzoate as light tan needles.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a4325b668a5848fe89889e8c378506c6
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08529671B2

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