Réaction #833530

Équation de réaction

n-butyl lithium

n-butyl lithium

chloroacetic acid

water

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

→

white crystalline material

Rendement 31.4%

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

Rendement 31.4%

Solvants

toluene

toluene

Conditions de réaction

Traitement

1. 1
   Autreequipped with a magnetic stirrer, an addition funnel, and a condenser with a nitrogen inlet
2. 2
   AutreAn exothermic reaction
3. 3
   TempératureThe contents were heated
4. 4
   Températureto reflux for about 20 hours
5. 5
   TempératureAfter cooling to room temperature
6. 6
   workup.STIRRINGstirred
7. 7
   AutreThe water phase was collected
8. 8
   Lavagewashed with ether (100 ml)
9. 9
   ExtractionThe cloudy solution was extracted twice with ether (100 ml)
10. 10
    Lavagethe combined ether solutions washed with brine (100 ml)
11. 11
    Séchagedried over anhydrous magnesium sulfate
12. 12
    AutreThe solvent was removed
13. 13
    Autrethe residue was recrystallized from a small amount of hexane

Mode opératoire

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.).

Source