Acetic Acid → 2-Methoxy-4-(2-nitroethenyl)-1-(phenylmethoxy)benzene

HRID 1884251

Reaktionsgleichung

Reaktionsgleichung von HRID 1884251
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:19]([CH3:22])([O-:21])=[O:20].C(O)(=O)C.C(N)CCC>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[CH:22][N+:19]([O-:21])=[O:20])=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 8007ButylamineHCID 755064-(Benzyloxy)-3-methoxybenzaldehyde

Produkt 1

HCID 158282-Methoxy-4-(2-nitroethenyl)-1-(phenylmethoxy)benzeneAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

23.1 g (95.7 mmol) of 4-benzyloxy-3-methoxybenzaldehyde, 8.76 g (143 mmol) of nitromethane and 250 ml of acetic acid were mixed and 7.07 g (96.7 mmol) of butylamine was added dropwise thereto. The mixture was refluxed for 2 hours by heating, and then cooled and poured into ice-water. The precipitated crystals were dissolved with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was washed with hexane and dried to give 17.0 g of 1-benzyloxy-2-methoxy-4-(2-nitrovinyl)benzene.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperatureby heating
  3. temperaturecooled
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. washThe residue was washed with hexane
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9a3a35f4a44f458b95c06c502bbd9a57
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06762321B2

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