Sodium Hydroxide → 3-(2,4-difluorophenyl)propanoic Acid

HRID 130607

Reaction equation

HRID 130607 reaction equation
[F:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].[OH-].[Na+].[H][H]>[Pd]>[F:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6035023-(2,4-Difluorophenyl)acrylic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 49863953-(2,4-difluorophenyl)propanoic AcidYield 85%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
100 °C

Procedure

The procedure was as in Example 5, but the 2,4-difluorocinnamic acid obtained was not isolated. The aqueous-acidic product suspension obtained was rendered alkaline using sodium hydroxide solution and treated with 2 g of Pd/C (5% strength) at 50° C. with further stirring and heated to 100° C. It was then pressurized to 5 bar of hydrogen. After constant pressure had been achieved, it was cooled to room temperature, the pressure was released and the palladium catalyst was filtered off. The alkaline product solution was acidified with sulfuric acid and the product precipitate was isolated by filtration. After drying in vacuo, 95.0 g of 3-(2,4-difluorophenyl)propionic acid (85% of theory) were obtained.

Workup

  1. customwas not isolated
  2. customThe aqueous-acidic product suspension obtained
  3. temperatureit was cooled to room temperature
  4. filtrationthe palladium catalyst was filtered off
  5. customthe product precipitate was isolated by filtration
  6. customAfter drying in vacuo

Sources & evidence

ORD record
ord-9e4e1d0e34434b238fee93adb46af9bf
Source dataset
uspto-grants-2008_06
Patent number
US07381832B2

Linked notes

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