Methanol → 4-(3-Chloropyridin-2-yl)benzaldehyde
Reaction equation
[Cl:1][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C[OH:16]>>[Cl:1][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[O:16])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1Participants
3
Conditions
- Temperature
- 25 °C
Procedure
{circle around (2)} 100 g (0.49 mol) of 3-chloro-2-para-tolylpyridine was dissolved in 0.5 L of methanol in a reactor. A solution of 537 g (0.98 mol) of ceric ammonium nitrate in 1 L of methanol was added dropwise, and the mixture was refluxed for 4˜6 hours. The reaction solution was cooled to 25° C. and concentrated under reduced pressure. A 10% sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure, yielding 4-(3-chloropyridin-2-yl)benzaldehyde as represented below in a 60% yield.