Reaktion #439448

Reaktionsgleichung

6-bromo2-naphthol

6-chloro-1-hexanol

potassium carbonate

potassium iodide

HCl

→

6-(6bromo-naphthalen-2-yloxy)hexan-1-ol

Ausbeute 76.7%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was then cooled
2. 2
   Extraktionextracted with ether (3×200 ml)
3. 3
   WaschenThe combined ether extracts were washed with saturated NaCl solution (200 ml)
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Sonstigeevaporated
6. 6
   Sonstigeto give a brownish oil
7. 7
   Filtrationfiltered through a silica gel column (150 g,)
8. 8
   Sonstigeto give a brownish solid
9. 9
   SonstigeThe brown solid was recrystallised from hexane/dichloromethane (9/1)

Vorschrift

A mixture of 6-bromo2-naphthol (22.30 g), 6-chloro-1-hexanol (20.50 g), potassium carbonate (20.50 g) and potassium iodide (1.50 g) in dimethylformamide (DMF, 100 ml) was heated at 100° C for 4 h. The mixture was then cooled and poured into 150 ml of HCl (3N) and extracted with ether (3×200 ml). The combined ether extracts were washed with saturated NaCl solution (200 ml), dried over magnesium sulfate, evaporated to give a brownish oil and filtered through a silica gel column (150 g,) using dichloromethane as eluent to give a brownish solid. The brown solid was recrystallised from hexane/dichloromethane (9/1) to give 24.8 g of 6-(6bromo-naphthalen-2-yloxy)hexan-1-ol as white needles.

Quelle