Benzene → Methyl 4-[(1Z)-2-nitropenta-1-enyl]benzoate

HRID 351348

Reaktionsgleichung

Reaktionsgleichung von HRID 351348
C(N)CCC.[CH:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)=O.C1C=CC=CC=1.[N+:24]([CH2:27][CH2:28][CH2:29][CH3:30])([O-:26])=[O:25]>C(O)(=O)C.O>[N+:24](/[C:27](/[CH2:28][CH2:29][CH3:30])=[CH:6]\[C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)([O-:26])=[O:25]

Komponenten

7

Edukt 4

HCID 241BenzeneHCID 8007ButylamineHCID 123021-NitrobutaneHCID 15294Methyl 4-Formylbenzoate

Produkt 1

HCID 58807290Methyl 4-[(1Z)-2-nitropenta-1-enyl]benzoateAusbeute 46,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

n-Butylamine (8.31 ml, 84.1 mmol) and methyl 4-formylbenzoate (10.6 g, 64.7 mmol) was heated with reflux benzene (50 ml) in a Dean-Stark trap until a theoretical amount of water was recovered. The solvent was evaporated under reduced pressure. To the residue were added glacial acetic acid (30 ml) and nitrobutane (10.0 g, 97.0 mmol), and the mixture was stirred at 110° C. for 4 hrs. and allowed to cool to room temperature. The insoluble materials were filtered off and dried to give the title compound (7.53 g) as a pale-yellow powder.

Aufarbeitung

  1. customwas recovered
  2. customThe solvent was evaporated under reduced pressure
  3. temperatureto cool to room temperature
  4. filtrationThe insoluble materials were filtered off
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-55c2bf59c9ae48ebafa26b9b38aadab3
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183415B2

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