Acetic Acid → HCID 19804299, compound

HRID 1681846Notes

Reaction equation

HRID 1681846 reaction equation
[OH-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]=O)[CH:4]=1.[CH:11](=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(O)(=O)C>CO>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5](/[CH:9]=[C:12](\[CH2:13][CH2:14][CH2:15][CH3:16])/[CH:11]=[O:17])[CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6184HexanalHCID 103713-PyridinecarboxaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 19804299HCID 19804299, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.0 g (0.15 mol) of sodium hydroxide were added to a solution of 160.5 g (1.5 mol) of pyridine-3-carbaldehyde in 750 ml of methanol. Thereafter, 150.0 g (1.5 mol) of hexanal were added dropwise in the course of 3 hours at room temperature. Stirring was carried out for 1 hour, the pH was brought to 6 with acetic acid and the solvent was then evaporated under reduced pressure. The residue was taken up in a water/dichloromethane mixture and the organic phase was washed with water, dried over sodium sulfate and evaporated down under reduced pressure. Distillation gave 190 g (67% of theory) of E-2-(3-pyridylmethylidene)-hexanal as a yellow oil of boiling point 132°-134° C./2 mbar.

Workup

  1. customthe solvent was then evaporated under reduced pressure
  2. washthe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated down under reduced pressure
  5. distillationDistillation

Sources & evidence

ORD record
ord-53410bcb0a874c1db3c36050a49c138b
Source dataset
uspto-grants-1992_12
Patent number
US05175167

Reaction notes

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