Malonic Acid → (E)-2-Nonenoic Acid

HRID 1657940Notes

Reaction equation

HRID 1657940 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3](O)=O.[CH:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]C>N1C=CC=CC=1>[C:1]([OH:7])(=[O:6])/[CH:2]=[CH:3]/[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 867Malonic AcidHCID 8130Heptanal

Product 1

HCID 5312586(E)-2-Nonenoic AcidYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Malonic acid (342 g, 3.3 mole) is dissolved in 555 ml of dry pyridine (slightly exothermic). The mixture is cooled in ice water and n-heptaldehyde (342 g, 3.0 mole) is added with stirring. After the addition is complete, the ice bath is removed and the mixture allowed to stand at room temperature for 60 hours, and then heated on a steam bath for 8 hours. The reaction mixture is poured onto an equal volume of water. The organic layer is separated, washed with 900 ml 25% HCl, taken up in benzene, washed with water and dried. Distillation under vacuum gave trans-2-nonenoic acid, b.p. 123°C/2 mm, 297 g, 64% yield.

Workup

  1. additionAfter the addition
  2. customthe ice bath is removed
  3. temperatureheated on a steam bath for 8 hours
  4. additionThe reaction mixture is poured onto an equal volume of water
  5. customThe organic layer is separated
  6. washwashed with 900 ml 25% HCl
  7. washwashed with water
  8. customdried
  9. distillationDistillation under vacuum

Sources & evidence

ORD record
ord-98979025175246ae8348b0f440568975
Source dataset
uspto-grants-1976_06
Patent number
US03962321

Reaction notes

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