Reaction #5380

Reaction equation

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

octyl iodide

potassium hydroxide

butanol

→

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

Yield 56.6%

Solvents

water

Conditions

Workup

1. 1
   Temperatureby refluxing for 310 minutes
2. 2
   Extractionextracted from ethyl acetate
3. 3
   Otherto obtain an organic layer
4. 4
   WashThe organic layer was washed with water
5. 5
   Dryingdried with mirabilite
6. 6
   Otherdried under reduced pressure
7. 7
   Otherto obtain a resultant
8. 8
   OtherThe resultant was recrystallized from ethylacetate
9. 9
   Otherto obtain a crystal
10. 10
    FiltrationThe crystal was filtered
11. 11
    Otherpurified by silica gel column chromatography (eluent: toluene)
12. 12
    Otherrecrystallized from acetone

Procedure

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