Citric Acid → (E)-2-Nonenal

HRID 1657939Notes

Reaction equation

HRID 1657939 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([CH2:8][C:9]([OH:11])=O)(C(O)=O)O>CO>[CH:9](=[O:11])/[CH:8]=[CH:3]/[CH2:2][CH2:1][CH2:1][CH2:2][CH2:3][CH3:8]

Participants

3

Reactant 1

HCID 311Citric Acid

Product 1

HCID 5283335(E)-2-Nonenal

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Twenty to 30 ml of the recovered acetal is mixed with an equal volume of 50% citric acid solution and boiled gently in a Claisen flask. Methanol is allowed to boil off until the distillate temperature reaches 95°F , at which point distillation is stopped. The flask contents are 2X water washed, followed by a 5% sodium carbonate solution. The resulting oil is vacuum distilled to yield relatively pure trans-2-nonenal. Further purification is obtained, if desired, by gas chromatography.

Workup

  1. distillationreaches 95°F , at which point distillation
  2. washwashed
  3. distillationdistilled

Sources & evidence

ORD record
ord-e2fd3e0e04b848c983c39328a432d381
Source dataset
uspto-grants-1976_06
Patent number
US03962321

Reaction notes

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