반응 #833530

반응 방정식

n-butyl lithium

n-butyl lithium

chloroacetic acid

water

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

→

white crystalline material

수율 31.4%

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

수율 31.4%

용매

toluene

toluene

반응 조건

후처리

1. 1
   기타equipped with a magnetic stirrer, an addition funnel, and a condenser with a nitrogen inlet
2. 2
   기타An exothermic reaction
3. 3
   온도The contents were heated
4. 4
   온도to reflux for about 20 hours
5. 5
   온도After cooling to room temperature
6. 6
   workup.STIRRINGstirred
7. 7
   기타The water phase was collected
8. 8
   세척washed with ether (100 ml)
9. 9
   추출The cloudy solution was extracted twice with ether (100 ml)
10. 10
    세척the combined ether solutions washed with brine (100 ml)
11. 11
    건조dried over anhydrous magnesium sulfate
12. 12
    기타The solvent was removed
13. 13
    기타the residue was recrystallized from a small amount of hexane

실험 절차

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.).

출처