Reaction #833530

Reaction equation

n-butyl lithium

n-butyl lithium

chloroacetic acid

water

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

→

white crystalline material

Yield 31.4%

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

Yield 31.4%

Solvents

toluene

toluene

Conditions

Workup

1. 1
   Otherequipped with a magnetic stirrer, an addition funnel, and a condenser with a nitrogen inlet
2. 2
   OtherAn exothermic reaction
3. 3
   TemperatureThe contents were heated
4. 4
   Temperatureto reflux for about 20 hours
5. 5
   TemperatureAfter cooling to room temperature
6. 6
   workup.STIRRINGstirred
7. 7
   OtherThe water phase was collected
8. 8
   Washwashed with ether (100 ml)
9. 9
   ExtractionThe cloudy solution was extracted twice with ether (100 ml)
10. 10
    Washthe combined ether solutions washed with brine (100 ml)
11. 11
    Dryingdried over anhydrous magnesium sulfate
12. 12
    OtherThe solvent was removed
13. 13
    Otherthe residue was recrystallized from a small amount of hexane

Procedure

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