Reaktion #595096

Reaktionsgleichung

4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde

2-chloroethyl ethyl ether

potassium carbonate

potassium iodide

→

title compound

Ausbeute 89.0%

4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-carbaldehyde

Ausbeute 89.0%

Lösungsmittel

N,N-dimethylformamide

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with ethyl acetate
2. 2
   WaschenThe extract was washed with saturated brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe residue was purified by silica gel column chromatography (5%-25% ethyl acetate/hexane)

Vorschrift

To a solution of 4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (8.52 g, 37.7 mmol) and 2-chloroethyl ethyl ether (6.15 g, 56.6 mmol) in N,N-dimethylformamide (40 mL) were added potassium carbonate (6.25 g, 45.2 mmol) and potassium iodide (1.25 g, 7.54 mmol), and the mixture was stirred at 80° C. for 18 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-25% ethyl acetate/hexane) to give the title compound (10.0 g, yield 89%) as a colorless oil.

Quelle