Réaction #1658

Équation de réaction

3-(4-methylbenzoyl)propionic acid

aluminum chloride

chlorine

→

3-(3,5-dichloro-4-methylbenzoyl)propionic acid

Rendement 44.2%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Autrewas bubbled in slowly at 0° C
3. 3
   workup.ADDITIONAfter 6 hours the reaction mixture was poured into a mixture of hydrochloric acid and ice
4. 4
   Extractionextracted with methylene chloride (3×150 ml)
5. 5
   Lavagethe combined organic layers were washed with water
6. 6
   Autredried
7. 7
   Autreevaporated under vacuum

Mode opératoire

To a mixture of 3-(4-methylbenzoyl)propionic acid (7.5 g) and methylene chloride (250 ml) was added slowly portionwise aluminum chloride (15 g) at 0° C. After the addition was completed chlorine gas was bubbled in slowly at 0° C. After 6 hours the reaction mixture was poured into a mixture of hydrochloric acid and ice and extracted with methylene chloride (3×150 ml), the combined organic layers were washed with water, dried and evaporated under vacuum yielding 3-(3,5-dichloro-4-methylbenzoyl)propionic acid as a yellow solid (4.5 g).

Source