p-Toluenesulfonic acid → HCID 11020281, compound

HRID 1165765Notes

Reaction equation

HRID 1165765 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][N:3]=1.C([O-])([O-])[O:11][CH2:12][CH3:13].[C:16]1(C)C=CC(S(O)(=O)=O)=C[CH:17]=1>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]([O:11][CH2:12][CH3:13])[O:9][CH2:16][CH3:17])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 27629942-Chloro-4-pyridinecarboxaldehydeHCID 53630039Ethylorthoformate

Product 1

HCID 11020281HCID 11020281, compoundYield 855.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

60 g of 2-chloro-4-pyridinecarboxaldehyde and 90 g of ethyl orthoformate were dissolved in 600 ml of ethanol, and 7 g of p-toluenesulfonic acid was added. The mixture was refluxed for 1 hour. After cooling, the reaction solution was concentrated. The concentrate was taken into ethyl acetate, washed with a saturated aqueous solution of sodium hydrogen carbonate and then a saturated aqueous solution of sodium chloride, and dried. The solvent was then evaporated. The residue was distilled under reduced pressure to give 75 g (yield 82%) of 2-chloro-4-diethoxymethylpyridine.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. concentrationthe reaction solution was concentrated
  4. washwashed with a saturated aqueous solution of sodium hydrogen carbonate
  5. dry with materiala saturated aqueous solution of sodium chloride, and dried
  6. customThe solvent was then evaporated
  7. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-19042fd09358470eb1246b3c0f0cdef8
Source dataset
uspto-grants-1990_03
Patent number
US04912101

Reaction notes

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