3-(2,4-Difluorophenyl)acrylic Acid → 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].[H][H]>O1CCCC1.[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 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
105 g of 2,4-difluorocinnamic acid from Example 5 were dissolved in 450 ml of tetrahydrofuran and reacted with 5 g of palladium on active carbon with stirring at 100° C. and a hydrogen pressure of 50 bar. After a constant pressure had been achieved, the mixture was cooled to room temperature, the pressure was released, the palladium catalyst was filtered off and the solvent was removed by distillation. After drying in vacuo, 104.1 g of 3-(2,4-difluorophenyl)-propionic acid (98% of theory; melting point: 100-102° C.) were obtained.
Workup
- temperaturethe mixture was cooled to room temperature
- filtrationthe palladium catalyst was filtered off
- customthe solvent was removed by distillation
- customAfter drying in vacuo
Sources & evidence
- ORD record
- ord-e94d579ec5ab4dc48ad69c7ff6af0c3c
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06956129B2
Reaction notes
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