Hydrochloric Acid → 3-(4-Fluoro-3-methoxyphenyl)propanoic acid
Reaction equation
C([O:3][C:4](=[O:16])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][CH3:15])[CH:8]=1)C.[OH-].[Na+].Cl>C(OCC)(=O)C.C(O)C.[C].[Pd]>[F:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:4]([OH:16])=[O:3])=[CH:8][C:9]=1[O:14][CH3:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 3-(4-fluoro-3-methoxyphenyl)acrylic acid ethyl ester (4.54 g) in ethyl acetate (20 mL)-ethanol (20 mL) was added 10% percent palladium-carbon (450 mg). After stirring under hydrogen gas atmosphere for 2.5 hours, the metal catalyst was removed by filtration, the solvent was removed by evaporation, and an oily substance (4.64 g) was obtained. This was dissolved in a solution of ethanol (40 mL), an aqueous solution of 5N sodium hydroxide was added, and the solution was stirred at room temperature for 30 minutes. After the solution was acidified by adding 5N hydrochloric acid (21 mL), the solid precipitated. After diluting with water, the solid was collected by filtration, dried by aeration, and a colorless solid (3.4 g) was obtained.
Workup
- customthe metal catalyst was removed by filtration
- customthe solvent was removed by evaporation
- customan oily substance (4.64 g) was obtained
- stirringthe solution was stirred at room temperature for 30 minutes
- customthe solid precipitated
- additionAfter diluting with water
- filtrationthe solid was collected by filtration
- customdried by aeration
Sources & evidence
- ORD record
- ord-1ee790a2cc374549946077db4673c300
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07217723B2
Reaction notes
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