Reaktion #95205

Reaktionsgleichung

alpha-hydroxyacetanilide

4,4'-bis(N,N-dimethylamino)benzhydrol

methyl ether

tetrahydrofuran

→

2-Bis(p-dimethylaminophenyl)Methoxy Acetanilide

Lösungsmittel

n-hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Filtrationthe reaction mixture was filtered hot
3. 3
   Temperaturthe filtrate chilled
4. 4
   SonstigeYellow-green crystals formed
5. 5
   Sonstigewhich were recrystallized from 30 ml petroleum ether/15 ml acetone
6. 6
   Sonstigeto give a white solid, mp 118°-128° C.

Vorschrift

A solution of alpha-hydroxyacetanilide (3.62 g, 0.024 mole), 4,4'-bis(N,N-dimethylamino)benzhydrol, methyl ether (6.81 g, 0.024 mole) 50 ml of tetrahydrofuran, 153 ml of n-hexane, and one drop of methanesulfonic acid was refluxed for 11 hours, during which time an additional 300 ml of solvent was added. The blue-green solution was decolorized with 4 drops of tetramethylguanidine and the reaction mixture was filtered hot and the filtrate chilled. Yellow-green crystals formed, which were recrystallized from 30 ml petroleum ether/15 ml acetone to give a white solid, mp 118°-128° C.

Quelle