Hydrochloric Acid → 3-[4-(2-Fluorophenyl)benzoyl]propanoic acid

HRID 1491965Notes

Reaction equation

HRID 1491965 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.Cl>ClC(Cl)C>[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 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 675792-FluorobiphenylHCID 6451240Aluminum(III) Chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

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

Workup

  1. additionwere added
  2. additioncontaining ice
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-0e962b3451d44d9785f54d4b747f2977
Source dataset
uspto-grants-1994_12
Patent number
US05371225

Reaction notes

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