(2-Chloro-5-(pyridin-2-yl)phenyl)methanol → 2-Chloro-5-(pyridin-2-yl)benzaldehyde

HRID 594221Notes

Reaction equation

HRID 594221 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH2:14][OH:15]>C1COCC1.O=[Mn]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH:14]=[O:15]

Participants

4

Reactant 1

HCID 69083854(2-Chloro-5-(pyridin-2-yl)phenyl)methanol

Product 1

HCID 866956092-Chloro-5-(pyridin-2-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-chloro-5-(pyridin-2-yl)phenyl)methanol (129 mg; 0.72 mmol) in anh. THF (7 ml) was treated with MnO2 (975 mg; 11.22 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 6.5 h. The resulting reaction mixture was then filtered over celite, and the separated solids were washed with THF. The filtrate was concentrated to dryness under reduced pressure giving 2-chloro-5-(pyridin-2-yl)benzaldehyde as a yellow oil. LC-MS (conditions A): tR=0.43 min.; no ionisation.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas then filtered over celite
  3. washthe separated solids were washed with THF
  4. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e499c14df9794d05a477fcdfd2438064
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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