4-(4-Fluoro-3-methylphenyl)-4-oxobutanoic acid → 4-(4-Fluoro-3-methylphenyl)butanoic acid

HRID 1458306Notes

Reaction equation

HRID 1458306 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[CH3:15].[H][H]>[C].[Pd].CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[CH3:15]

Participants

5

Reactant 2

HCID 64854434-(4-Fluoro-3-methylphenyl)-4-oxobutanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 64970724-(4-Fluoro-3-methylphenyl)butanoic acidYield 87.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

In a 50-ml autoclave, 1.0 g of 4-(4-fluoro-3 -methylphenyl)-4-oxobutanoic acid and 2.5 ml of methanol were charged, followed by the addition of 0.1 g of 10% palladium-carbon. After hydrogen pressure was increased to 30 kg/cm2 at room temperature, the resulting mixture was stirred at 50° C. for 3.5 hours. After the completion of the reaction, the reaction mixture was filtered, followed by washing with methanol. The filtrate was thereafter concentrated under reduced pressure. Water was added to the residue so obtained. The crystals so precipitated were filtered, washed with water and dried under reduced pressure, whereby 0.82 g of the title compound was obtained.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. washby washing with methanol
  4. concentrationThe filtrate was thereafter concentrated under reduced pressure
  5. additionWater was added to the residue
  6. customso obtained
  7. customThe crystals so precipitated
  8. filtrationwere filtered
  9. washwashed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-fb4f002e781a478cbe1ffd35a52ac052
Source dataset
uspto-grants-1998_12
Patent number
US05849945

Reaction notes

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