Hydrochloric Acid → 4-(4-Fluoro-3-methylphenyl)-4-oxobutanoic acid

HRID 2257881Notes

Reaction equation

HRID 2257881 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]>>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[CH:16][C:15]=1[CH3:20]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 72412-FluorotolueneHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 64854434-(4-Fluoro-3-methylphenyl)-4-oxobutanoic acid

Conditions

Temperature
80 °C

Procedure

200 gm of succinic anhydride and 800 gm of aluminum chloride were added to 250 ml of 2-fluorotoluene, and the mixture was heated at 80° C. for 1 hour. Upon the addition of 5 l of 1% cold hydrochloric acid aqueous solution, the reaction mixture was extracted with ethyl acetate, washed with 1N hydrochloric acid and water, and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 345 gm of the title compound.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with 1N hydrochloric acid and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5b48be5a41f44069b60cde144a5c607f
Source dataset
uspto-grants-1997_08
Patent number
US05658920

Reaction notes

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