Acetaminophen → {4-[(2,4-Dichlorobenzyl)oxy]phenyl}amine

HRID 26117

Reaktionsgleichung

Reaktionsgleichung von HRID 26117
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6]C(=O)C)=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:14]=1[CH2:15]Cl.[O-]CC.[Na+].[OH-].[K+]>C(O)C>[Cl:12][C:13]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:14]=1[CH2:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:6])=[CH:10][CH:11]=1

Komponenten

6

Edukt 4

HCID 1983AcetaminophenHCID 72122,4-Dichlorobenzyl chlorideHCID 14797Potassium HydroxideHCID 2723922Sodium ethoxide

Produkt 1

HCID 11579870{4-[(2,4-Dichlorobenzyl)oxy]phenyl}amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

In ethanol, p-hydroxyacetoanilide is reacted with 2,4-dichlorobenzyl chloride in the presence of sodium ethoxide and the resultant 4-(2,4-dichlorobenzyloxy)-acetoanilide is treated with potassium hydroxide in ethanol, whereby 4-(2,4-dichlorobenzyloxy)-aniline is obtained as crystals melting at 70°-71° C. In a similar manner, the following compounds can be prepared from the corresponding substituted benzyl halide derivatives.

Quellen und Nachweise

ORD-Eintrag
ord-4c19737ec5074348aae7fcac049d1513
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04148625

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