Methanol → 4-(3-Chloropyridin-2-yl)benzaldehyde

HRID 578590Notes

Reaction equation

HRID 578590 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]=1

Participants

3

Reactant 2

HCID 887Methanol2×HCID 207099363-Chloro-2-(p-tolyl)pyridine

Product 1

HCID 534262384-(3-Chloropyridin-2-yl)benzaldehydeYield 60%

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.

Workup

  1. temperaturethe mixture was refluxed for 4˜6 hours
  2. concentrationconcentrated under reduced pressure
  3. additionA 10% sodium bicarbonate solution was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c844a60fb1634e37b5a567e14fc4bad1
Source dataset
uspto-grants-2015_05
Patent number
US09040572B2

Reaction notes

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