Reaktion #1517

Reaktionsgleichung

p-toluylic acid

N-bromosuccinimide

→

4-bromomethylbenzoic acid

Ausbeute 65.3%

Lösungsmittel

carbon tetrachloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigea reaction
2. 2
   Temperaturunder reflux for 2 hours
3. 3
   SonstigeAfter completion of the reaction
4. 4
   Temperaturthe reaction mixture was cooled in ice bath
5. 5
   FiltrationThe deposited crystalline product was collected by filtration, which
6. 6
   Waschenwas then washed with hexane and water
7. 7
   Sonstigeby drying
8. 8
   SonstigeThe resultant crystalline product was recrystallized from ethanol
9. 9
   Sonstigeto obtain

Vorschrift

39.7 g (287 mmol) of p-toluylic acid, 51.2 g (287 mmol) of N-bromosuccinimide and 2.8 g (11.5 mmol) of dibenzoyl peroxide were suspended in 350 ml of carbon tetrachloride. Then, the resultant mixture was heated with vigorously stirring to perform a reaction under reflux for 2 hours. After completion of the reaction, the reaction mixture was cooled in ice bath. The deposited crystalline product was collected by filtration, which was then washed with hexane and water, followed by drying. The resultant crystalline product was recrystallized from ethanol to obtain 40.3 g of 4-bromomethylbenzoic acid as a white needle crystal (isolated yield: 65%).

Quelle