Methane → 3-(3-Phenylpropyl)aniline

HRID 905148Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 905148
[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 no further hydrogen is absorbed. When the mixture has cooled, some of the acetic acid is distilled off, the residue is rendered alkaline with sodium hydroxide solution and extracted by shaking with ether, the organic phase is dried over sodium sulfate and filtered, the solvent is stripped off and the residue is distilled. 150 g of 3-(3-phenylpropyl)-aniline of boiling point 148° C./0.2 mbar are obtained.

Aufarbeitung

  1. customis absorbed
  2. temperatureWhen the mixture has cooled
  3. distillationsome of the acetic acid is distilled off
  4. extractionextracted
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. distillationthe residue is distilled

Quellen und Nachweise

ORD-Eintrag
ord-118962f8141344bbbecf904263d15b7f
Quelldatensatz
uspto-grants-1983_12
Patentnummer
US04422871

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