Malonic Acid → (E)-2-Nonenoic Acid

HRID 1657940ノート

反応式

HRID 1657940 の反応式
[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]

参加物

4

反応物 2

HCID 867Malonic AcidHCID 8130Heptanal

生成物 1

HCID 5312586(E)-2-Nonenoic Acid収率 64%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-98979025175246ae8348b0f440568975
出典データセット
uspto-grants-1976_06
特許番号
US03962321

反応ノート

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