Succinic anhydride → 3-(4-Fluorobenzoyl)propionic acid

HRID 339171Notes

Reaction equation

HRID 339171 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3].[C:12]1(=[O:18])[O:17][C:15](=[O:16])[CH2:14][CH2:13]1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 10008FluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1013593-(4-Fluorobenzoyl)propionic acidYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Fluorobenzene (50 mL, 530 mmol) and aluminum trichloride (156 g, 1.17 mol) were added to 500 mL of methylene chloride, and the reaction mixture was stirred. Succinic anhydride (50 g, 500 mmol) was added to the stirring reaction mixture all at once, and the reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched by cautious addition of 10% HCl, and the reaction mixture was added to 500 mL of water. The aqueous mixture was extracted twice with 250 mL of methylene chloride, and the combined organic layers were dried (MgSO4), and evaporated under reduced pressure to give 62 g (316 mmol, 59.6%) of 4-(4-fluoro-phenyl)-4-oxo-butyric acid as a crude solid. MS: 197 (M+H)+.

Workup

  1. stirringwas stirred at room temperature for 2 hours
  2. customThe reaction was quenched by cautious addition of 10% HCl
  3. additionthe reaction mixture was added to 500 mL of water
  4. extractionThe aqueous mixture was extracted twice with 250 mL of methylene chloride
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9004b1506425438da73a4e1388601570
Source dataset
uspto-grants-2014_11
Patent number
US08889906B2

Reaction notes

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