Sodium Methoxide → 2,2',4'-Trifluoro-3-methoxybiphenyl-4-carbaldehyde
Reaction equation
[CH3:1][O-:2].[Na+].[F:4][C:5]1[C:10](F)=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7][C:6]=1[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21]>CO>[F:4][C:5]1[C:10]([O:2][CH3:1])=[C:9]([CH:12]=[O:13])[CH:8]=[CH:7][C:6]=1[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium methoxide (28% methanol solution, 5.64 g) was added at room temperature to a methanol (120 mL) solution of 2,2′,3,4′-tetrafluorobiphenyl-4-carbaldehyde (4.95 g), and the mixture was heated to reflux for 16 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and then, the solvent was distilled off under reduced pressure. The obtained residue was diluted with ethyl acetate and water, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline in this order and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure to obtain the title compound (5.14 g).
Workup
- temperaturethe mixture was heated
- temperatureto reflux for 16 hours in a nitrogen atmosphere
- distillationthe solvent was distilled off under reduced pressure
- additionThe obtained residue was diluted with ethyl acetate and water
- extractionfollowed by extraction with ethyl acetate
- washThe obtained organic layer was washed with water and saturated saline in this order
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-1a30248d054a40ff97bf48a168611ffe
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09353108B2
Reaction notes
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