Sodium Hydroxide → Phenethylamine, 4-(benzyloxy)-3-methoxy-

HRID 1884252

Reaktionsgleichung

Reaktionsgleichung von HRID 1884252
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[CH:22][N+:23]([O-])=O)=[CH:17][C:16]=1[O:26][CH3:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>O1CCCC1>[CH3:27][O:26][C:16]1[CH:17]=[C:18]([CH2:21][CH2:22][NH2:23])[CH:19]=[CH:20][C:15]=1[O:14][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 158282-Methoxy-4-(2-nitroethenyl)-1-(phenylmethoxy)benzeneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 200382Phenethylamine, 4-(benzyloxy)-3-methoxy-Ausbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

6.78 g (178.8 mmol) of lithium aluminum hydride and 200 ml of anhydrous tetrahydrofuran were mixed and an anhydrous tetrahydrofuran solution of 17.0 g (59.6 mmol) of 1-benzyloxy-2-methoxy-4-(2-nitrovinyl)benzene was added dropwise thereto over about 90 minutes under vigorous stirring. The mixture was refluxed for 2 hours by heating, and then cooled and aqueous sodium hydroxide solution was added to the mixture. The precipitates were filtered off with celite-precoated glass filter and the solvent was distilled off from the filtrate under reduced pressure. The residue was extracted with ethyl acetate, washed with saturated brine, dried over potassium carbonate and the solvent was distilled off under reduced pressure to give 13.67 g of crude 2-(3-methoxy-4-benzyloxyphenyl)ethylamine.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperatureby heating
  3. temperaturecooled
  4. filtrationThe precipitates were filtered off with celite-precoated glass
  5. filtrationfilter
  6. distillationthe solvent was distilled off from the filtrate under reduced pressure
  7. extractionThe residue was extracted with ethyl acetate
  8. washwashed with saturated brine
  9. dry with materialdried over potassium carbonate
  10. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7489f92746fb4d7ba0cec264447c0196
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06762321B2

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