Réaction #595096

Équation de réaction

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

2-chloroethyl ethyl ether

potassium carbonate

potassium iodide

→

title compound

Rendement 89.0%

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

Rendement 89.0%

Solvants

N,N-dimethylformamide

Water

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture was extracted with ethyl acetate
2. 2
   LavageThe extract was washed with saturated brine
3. 3
   Séchagedried over anhydrous magnesium sulfate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   AutreThe residue was purified by silica gel column chromatography (5%-25% ethyl acetate/hexane)

Mode opératoire

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.

Source