Succinic anhydride → 4-(3,4-Difluorophenyl)-4-oxobutanoic acid

HRID 2186871

Reaction equation

HRID 2186871 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[Cl-].[Al+3].[Cl-].[Cl-].[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19]>Cl>[F:12][C:13]1[CH:18]=[C:17]([C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5])[CH:16]=[CH:15][C:14]=1[F:19]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 97061,2-DifluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27583374-(3,4-Difluorophenyl)-4-oxobutanoic acidYield 31.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

45 gm of succinic anhydride and 130.7 gm of aluminum chloride were added to 57 gm of difluorobenzene, and the mixture was heated under reflux for 4 hours. Upon the addition of 200 ml of 1% hydrochloric acid aqueous solution, the reaction mixture was extracted with chloroform, washed. with water, and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was subjected to silica gel column chromatography using a chloroform-methanol (30:1) mixed solvent as an eluant to obtain fractions containing the target compound. The fractions were concentrated to produce 30 gm of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. extractionthe reaction mixture was extracted with chloroform
  4. washwashed
  5. dry with materialwith water, and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. additionmixed solvent as an eluant
  8. customto obtain fractions
  9. additioncontaining the target compound
  10. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-a61ce4c4721f488e9d2c6807bc3d71bf
Source dataset
uspto-grants-2002_06
Patent number
US06407115B1

Linked notes

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