3-Hydroxybenzyl alcohol → 3-(Pyridin-2-yloxy)benzaldehyde
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].Br[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
3-Hydroxybenzyl alcohol (1.0 g, 8.2 mmol) was dissolved in pyridine (20 mL). 2-Bromopyridine (1.6 g, 9.8 mmol) and potassium carbonate (2.3 g, 16.4 mmol) were added thereto, and then the mixture was stirred at 90° C. for 10 minutes. Copper oxide(II) (1.6 g, 20.5 mmol) was further added thereto, and the reaction mixture was heated under reflux for 2 days. The reaction solution was filtered, and concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 70:30) to give the title compound (1.0 mg, yield 61%).
Workup
- temperaturethe reaction mixture was heated
- temperatureunder reflux for 2 days
- filtrationThe reaction solution was filtered
- concentrationconcentrated under reduced pressure
- additionTo the residue was added water
- extractionthe mixture was extracted with ethyl acetate
- customThe extract was dried
- concentrationconcentrated under reduced pressure
- customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 70:30)
Sources & evidence
- ORD record
- ord-6c30dd5c1b6f42d292cc86e16b1882fc
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008525B2
Reaction notes
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