Reaktion #831101

Reaktionsgleichung

hydrochloric acid

vinylbenzyl chloride

magnesium

diethyl ether

CO2

→

4-vinylphenylacetic acid

Ausbeute 22.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture is refluxed for 1 hour
2. 2
   Extraktionextracted twice with ether
3. 3
   WaschenThe combined ether phases are then washed with 500 ml of water
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe resultant oil is recrystallized from a mixture of 50 ml of toluene and 150 ml of n-hexane

Vorschrift

5.3 g (220 mmol) of magnesium turnings are mixed with 150 ml of diethyl ether under an inert nitrogen atmosphere in a 250 ml three-neck round-bottom flask. 30.5 g (200 mmol) of vinylbenzyl chloride are then added, and the mixture is refluxed for 1 hour. CO2 is then passed into the suspension, cooled to 5° C., until no exothermicity can be detected with the aid of a thermometer (about 9 g). The mixture is then poured into 400 ml of 1N hydrochloric acid and extracted twice with ether. The combined ether phases are then washed with 500 ml of water, dried over magnesium sulfate and evaporated. The resultant oil is recrystallized from a mixture of 50 ml of toluene and 150 ml of n-hexane, giving 7.1 g (22% of theory) of 4-vinylphenylacetic acid as a white powder of melting point 94° C.

Quelle