Methane → 2-[(Pyridin-4-yl)methoxy]benzaldehyde

HRID 380182Notes

Reaction equation

HRID 380182 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[OH-].[K+].Cl.[N:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][CH:14]=1.C>CS(C)=O.C(OCC)(=O)C.O>[N:13]1[CH:18]=[CH:17][C:16]([CH2:19][O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[CH:1]=[O:9])=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 6998SalicylaldehydeHCID 14797Potassium HydroxideHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 167689982-[(Pyridin-4-yl)methoxy]benzaldehydeYield 62.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of salicylaldehyde (5 g, 40.9 mmol) in DMSO (75 mL) was treated with crushed potassium hydroxide (5.4 g, 81.8 mmol) and allowed to stir at room temperature for 1 hour. This was then treated with 4-picolyl chloride hydrochloride (6.8 g, 40.9 mmol) and the dark mixture allowed to stir overnight. The mixture was poured into water and extracted twice with ethyl acetate. The combined ethyl acetate extracts were washed with 5% NaOH, three times with water then with brine. Drying over MgSO4 and removal of the solvent under reduced pressure gave the crude product. This was taken up in ethyl acetate, treated with charcoal, filtered, and the solvent removed under reduced pressure to give 5.42 g (62.1%) of the product as an oil; MS-CI 214 (M+1).

Workup

  1. stirringto stir overnight
  2. extractionextracted twice with ethyl acetate
  3. washThe combined ethyl acetate extracts were washed with 5% NaOH, three times with water
  4. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  5. customgave the crude product
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e990cc9022ba4599a03f84423bda0d6f
Source dataset
uspto-grants-2001_10
Patent number
US06300501B1

Reaction notes

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