Réaction #5380

Équation de réaction

2-(6-hydroxy-2-naphthyl)-5-butylbenzooxazole

octyl iodide

potassium hydroxide

butanol

→

2-(6-octyloxy-2-naphthyl)-5-butylbenzooxazole

Rendement 56.6%

Solvants

water

Conditions de réaction

Traitement

1. 1
   Températureby refluxing for 310 minutes
2. 2
   Extractionextracted from ethyl acetate
3. 3
   Autreto obtain an organic layer
4. 4
   LavageThe organic layer was washed with water
5. 5
   Séchagedried with mirabilite
6. 6
   Autredried under reduced pressure
7. 7
   Autreto obtain a resultant
8. 8
   AutreThe resultant was recrystallized from ethylacetate
9. 9
   Autreto obtain a crystal
10. 10
    FiltrationThe crystal was filtered
11. 11
    Autrepurified by silica gel column chromatography (eluent: toluene)
12. 12
    Autrerecrystallized from acetone

Mode opératoire

In a 30ml round-bottom flask, 0.47 g (1.48 m mole) of 2-(6-hydroxy-2-naphthyl)-5-butylbenzooxazole, 0.43 g (1.79 m mole) of octyl iodide, 0.12 g (1.82 m mole) of potassium hydroxide and 5 ml of butanol were placed, followed by refluxing for 310 minutes. The reaction mixture was poured into water, extracted from ethyl acetate to obtain an organic layer. The organic layer was washed with water dried with mirabilite and dried under reduced pressure to obtain a resultant. The resultant was recrystallized from ethylacetate to obtain a crystal. The crystal was filtered, purified by silica gel column chromatography (eluent: toluene) and recrystallized from acetone to obtain 0.36 g of 2-(6-octyloxy-2-naphthyl)-5-butylbenzooxazole (Yield: 56.6%). ##STR190##

Source