Succinic anhydride → 3-[4-(2-Fluorophenyl)benzoyl]propanoic acid

HRID 264774Notes

Reaction equation

HRID 264774 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[C:5]1(=[O:11])[O:10][C:8](=[O:9])[CH2:7][CH2:6]1.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClC(Cl)C.Cl>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:20]=[CH:21][C:22]([C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:11])=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 675792-FluorobiphenylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 137582703-[4-(2-Fluorophenyl)benzoyl]propanoic acidYield 89%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Aluminum trichloride (6.2 g, 46.5 mmol) was suspended in 50 ml of dichloroethane, and 3.02 g (30.2 mmol) of succinic anhydride and 4.0 g (23.2 mmol) of 2-fluorobiphenyl were added thereto, followed by stirring the mixture at room temperature for 4 hours. The reaction solution was poured in hydrochloric acid containing ice, and extracted with chloroform. The organic layer was washed with water, and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was recrystallized from chloroform to obtain 5.6 g of the above-mentioned compound (yield 89%).

Workup

  1. additioncontaining ice
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-28286910cf354cf7a57fbfcb95e41098
Source dataset
uspto-grants-1997_07
Patent number
US05646283

Reaction notes

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