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

HRID 2186878Notes

Reaction equation

HRID 2186878 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 1 N hydrochloric acid and water, and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 345 gm of the title compound. NMR(CDCl3) δ: 1.89-1.97(2H, m), 2.24(3H, s), 2.36(2H, t, J=7.3 Hz), 2.60(2H, t, J=7.3 Hz), 6.84-6.99(3H, m).

Workup

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

Sources & evidence

ORD record
ord-226280a06ae6446db984cb7f54c67e84
Source dataset
uspto-grants-2002_06
Patent number
US06407115B1

Reaction notes

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