Sodium Hydroxide → 3-(2,4-difluorophenyl)propanoic Acid
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
Product 1
Reagents, catalysts & solvents 1
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
- customwas not isolated
- customThe aqueous-acidic product suspension obtained
- temperatureit was cooled to room temperature
- filtrationthe palladium catalyst was filtered off
- customthe product precipitate was isolated by filtration
- customAfter drying in vacuo
Sources & evidence
- ORD record
- ord-c386ccb93df94b4988013f7c5f7079df
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06956129B2
Reaction notes
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