Reaction #1658

Reaction equation

3-(4-methylbenzoyl)propionic acid

aluminum chloride

chlorine

→

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

Yield 44.2%

Solvents

methylene chloride

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Otherwas 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
   Washthe combined organic layers were washed with water
6. 6
   Otherdried
7. 7
   Otherevaporated under vacuum

Procedure

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