Methane → 3-(3-Phenylpropyl)aniline

HRID 1995477

Reaktionsgleichung

Reaktionsgleichung von HRID 1995477
[C:1]1([C:7](=O)[CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.C.[H][H]>C(O)(=O)C.[Pd]>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[NH2:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 297MethaneHCID 1118Sulfuric AcidHCID 948623-NitrochalconeHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 4273073-(3-Phenylpropyl)anilineAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

253 g of 1-phenyl-3-(3'-nitrophenyl)-prop-2-en-1-one are suspended in 2.5 liters of glacial acetic acid. 196 g of concentrated sulfuric acid and 10 g of 10% strength Pd on animal charcoal are added and the mixture is hydrogenated under 1.1 bar hydrogen pressure, at 65°-70° C., until hydrogen is no longer absorbed. When the mixture has cooled, part of the acetic acid is distilled off, the residue is rendered alkaline with sodium hydroxide solution and extracted with ether, the organic phase is dried with sodium sulfate and filtered, the solvent is distilled off and the residue is then distilled. 150 g of 3-(3-phenylpropyl)-aniline, of boiling point 148° C./0.2 mbar, are obtained.

Aufarbeitung

  1. customis no longer absorbed
  2. temperatureWhen the mixture has cooled
  3. distillationpart of the acetic acid is distilled off
  4. extractionextracted with ether
  5. dry with materialthe organic phase is dried with sodium sulfate
  6. filtrationfiltered
  7. distillationthe solvent is distilled off
  8. distillationthe residue is then distilled

Quellen und Nachweise

ORD-Eintrag
ord-ba290084dd3d4a58bcbfde730449839b
Quelldatensatz
uspto-grants-1983_09
Patentnummer
US04405358

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