Reacción #833530

Ecuación de reacción

n-butyl lithium

n-butyl lithium

chloroacetic acid

water

2-(5-norbornen-2-yl)-2-propanol

→

white crystalline material

Rendimiento 31.4%

Glycolic acid 2-(5-norbornen-2-yl)-2-propyl ether

Rendimiento 31.4%

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroequipped with a magnetic stirrer, an addition funnel, and a condenser with a nitrogen inlet
2. 2
   OtroAn exothermic reaction
3. 3
   TemperaturaThe contents were heated
4. 4
   Temperaturato reflux for about 20 hours
5. 5
   TemperaturaAfter cooling to room temperature
6. 6
   workup.STIRRINGstirred
7. 7
   OtroThe water phase was collected
8. 8
   Lavadowashed with ether (100 ml)
9. 9
   ExtracciónThe cloudy solution was extracted twice with ether (100 ml)
10. 10
    Lavadothe combined ether solutions washed with brine (100 ml)
11. 11
    Secadodried over anhydrous magnesium sulfate
12. 12
    OtroThe solvent was removed
13. 13
    Otrothe residue was recrystallized from a small amount of hexane

Procedimiento

2-(5-norbornen-2-yl)-2-propanol (15.20 g, 0.10 mole) (JSR Corp., Japan) and toluene (100 ml) were added to a three-necked 500 ml round bottomed flask equipped with a magnetic stirrer, an addition funnel, and a condenser with a nitrogen inlet. The addition funnel was charged with n-butyl lithium (1.6M in hexane, 62.50 ml, 0.10 mole). The n-butyl lithium was added drop wise while stirring at room temperature. An exothermic reaction occurred. Afterwards, chloroacetic acid (4.75 g, 0.05 mole) in toluene (100 ml) was added drop wise. The contents were heated to reflux for about 20 hours. After cooling to room temperature, water (200 ml) was added cautiously and stirred. The water phase was collected, washed with ether (100 ml) and neutralized with 2 molar hydrochloric acid solution. The cloudy solution was extracted twice with ether (100 ml) and the combined ether solutions washed with brine (100 ml) and dried over anhydrous magnesium sulfate. The solvent was removed and the residue was recrystallized from a small amount of hexane to give 3.3 g of white crystalline material (Melting Point: 48.5-49.50° C.).

Fuente