Dimethylformamide → 3-[4-(3-Phenylpropoxy)phenyl]propanenitrile

HRID 1665979Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665979
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])C#N)=[CH:4][CH:3]=1.[C:12]1([CH2:18][CH2:19][CH2:20]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:28][N:29](C)C=O>C(OCC)C>[C:12]1([CH2:18][CH2:19][CH2:20][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:11][C:28]#[N:29])=[CH:6][CH:7]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 895432-(4-Hydroxyphenyl)propanenitrile

Produkt 1

HCID 666906523-[4-(3-Phenylpropoxy)phenyl]propanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxyphenylpropanenitrile (5.25 g) in N,N-dimethyl formamide (40 mL), 3-phenylpropyl bromide (7.1 g) and potassium carbonate (14.79 g) were added, followed by stirring at room temperature for 16 hours. Then, the reaction mixture was diluted with diethyl ether and an organic layer was successively washed with water and brine. After the organic layer was dried, the solvent was concentrated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the title compound (8.54 g) having the following physical properties.

Aufarbeitung

  1. washan organic layer was successively washed with water and brine
  2. customAfter the organic layer was dried
  3. concentrationthe solvent was concentrated
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-6439ec32e24949e68911c5fe820d6d71
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039674B2

Notizen zur Reaktion

Wird geladen…