Potassium Iodide → 2-(pyridin-2-ylmethoxy)benzaldehyde

HRID 2057427Notes

Reaction equation

HRID 2057427 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Cl.Cl[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)(C)C>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 7711162-(pyridin-2-ylmethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

12.2 g of salicylaldehyde and 16.4 g of 2-(chloromethyl)-pyridine-hydrochloride are, after the addition of 55.2 g of potassium carbonate and 0.2 g of potassium iodide in 200 ml of isopropanol, refluxed for 12 hours with thorough stirring. The hot reaction mixture is filtered, and concentrated in vacuo. The residue is dissolved in 100 ml of chloroform, and the solution extracted with 2 N sodium hydroxide solution and then with water. The chloroform solution is subsequently dried over anhydrous sodium sulphate, and concentrated in vacuo. The oil remaining is dissolved in benzene, and filtered through 200 g. of aluminium oxide (2% water). The filtrates are concentrated by evaporation, and the residue distilled in high vacuum to obtain 2-(2-pyridylmethoxy)-benzaldehyde as colourless viscous oil, B.P. 135°-164°/0.04 Torr, which, after solidification, melts at 69°-71°. This substance is heated for 30 minutes at 300° in a nitrogen atomosphere; after cooling, it is dissolved in methylene chloride, and the solution filtered through aluminium oxide (2% water). From the filtrate there is obtained 2-(2-benzofuranyl)-pyridine in the form of yellowish crystals, M.P. 86°-87° (from isopropanol).

Workup

  1. temperaturerefluxed for 12 hours with thorough stirring
  2. filtrationThe hot reaction mixture is filtered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in 100 ml of chloroform
  5. extractionthe solution extracted with 2 N sodium hydroxide solution
  6. dry with materialThe chloroform solution is subsequently dried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo
  8. dissolutionThe oil remaining is dissolved in benzene
  9. filtrationfiltered through 200 g
  10. concentrationThe filtrates are concentrated by evaporation
  11. distillationthe residue distilled in high vacuum

Sources & evidence

ORD record
ord-42c40b8d23b14539b8d00fc2bbd9e1d8
Source dataset
uspto-grants-1980_07
Patent number
US04210655

Reaction notes

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