Malonic Acid → (E)-2-Nonenoic Acid

HRID 1657940노트

반응식

HRID 1657940 반응식
[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]

참가 물질

4

반응물 2

HCID 867Malonic AcidHCID 8130Heptanal

생성물 1

HCID 5312586(E)-2-Nonenoic Acid수율 64%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-98979025175246ae8348b0f440568975
출처 데이터셋
uspto-grants-1976_06
특허 번호
US03962321

반응 노트

불러오는 중…