Chlorine → 4-(3,5-Dichloro-4-methylphenyl)-4-oxobutanoic acid

HRID 2067

Reaction equation

HRID 2067 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])=[CH:4][CH:3]=1.[Cl-:15].[Al+3].[Cl-:17].[Cl-].ClCl>C(Cl)Cl>[Cl:15][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([Cl:17])[C:2]=1[CH3:1])[C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7]

Participants

5

Reactant 3

HCID 24526ChlorineHCID 2441624-(4-Methylphenyl)-4-oxobutanoic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 125335864-(3,5-Dichloro-4-methylphenyl)-4-oxobutanoic acidYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. additionAfter the addition
  2. customwas bubbled in slowly at 0° C
  3. additionAfter 6 hours the reaction mixture was poured into a mixture of hydrochloric acid and ice
  4. extractionextracted with methylene chloride (3×150 ml)
  5. washthe combined organic layers were washed with water
  6. customdried
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-d16063bc2b004a4189a712a254c9912b
Source dataset
uspto-grants-1998_03
Patent number
US05728694

Linked notes

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