Reaction #94408

Reaction equation

ammonium chloride

magnesium

methallyl chloride

2-acetyl-3,3-dimethyl-5-norbornene

→

oil

Yield 106.5%

ALPHA-METHALLYL-ALPHA,3,3-TRIMETHYL-5-NORBORNENE-2-METHANOL

Yield 106.5%

Solvents

diethyl ether

Conditions

Workup

1. 1
   OtherInto a 1 liter reaction flask
2. 2
   Otherequipped with a reflux condenser
3. 3
   Otherthermometer, stirrer, dropping
4. 4
   Otherfunnel and nitrogen inlet tube are placed
5. 5
   workup.STIRRINGThe mixture is stirred
6. 6
   Temperatureat reflux for one-half hour
7. 7
   WashThe organic layer is washed with water
8. 8
   Dryingdried over magnesium sulfate
9. 9
   FiltrationThe mixture is then filtered
10. 10
    Otherthe solvent evaporated

Procedure

Into a 1 liter reaction flask equipped with a reflux condenser, thermometer, stirrer, dropping funnel and nitrogen inlet tube are placed 12 g (0.5 moles) of magnesium turnings and 250 cc anhydrous diethyl ether. Over a 2 hour period, 45.3 g (0.5 moles) of methallyl chloride is added. The Girgnard solution is stirred for 1/2 hour and 28 g of 2-acetyl-3,3-dimethyl-5-norbornene is added over a 20 minute period. The mixture is stirred at reflux for one-half hour and then is hydrolyzed by the addition of saturated ammonium chloride solution. The organic layer is washed with water and dried over magnesium sulfate. The mixture is then filtered and the solvent evaporated to yield 40 g of an oil, which is then fractionated on a micro Vigreux column after adding thereto 5 g Primol® and a trace quantity of Ionox®.

Source