2-Methyl-2-(pent-4-yn-1-yl)propanedioicacid → 2-Methylhept-6-ynoic acid

HRID 1197364

Reaktionsgleichung

Reaktionsgleichung von HRID 1197364
[CH3:1][C:2]([CH2:9][CH2:10][CH2:11][C:12]#[CH:13])(C(O)=O)[C:3]([OH:5])=[O:4]>C(#N)C>[CH3:1][CH:2]([CH2:9][CH2:10][CH2:11][C:12]#[CH:13])[C:3]([OH:5])=[O:4]

Komponenten

3

Edukt 1

HCID 193733782-Methyl-2-(pent-4-yn-1-yl)propanedioicacid

Produkt 1

HCID 193732982-Methylhept-6-ynoic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2-methyl-2-(pent-4-ynyl)malonic acid (5.7 g) and cuprous oxide (0.22 g) in acetonitrile (150 ml) was heated to reflux, under a nitrogen atmosphere, for 4.25 hours. The solvent was removed under reduced pressure and water (50 ml) was added to the residue followed by sufficient concentrated hydrochloric acid to hydrolyse the copper salts. The resulting aqueous phase was extracted with diethyl ether and the organic extracts were washed with water and brine before drying over anhydrous magnesium sulphate and evaporation in vacuo. 2-Methylhept-6-ynoic acid (3.6 g) was obtained as a colourless oil after distillation (b.p. 150°-165°, 0.5 mm Hg).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux, under a nitrogen atmosphere, for 4.25 hours
  3. customThe solvent was removed under reduced pressure and water (50 ml)
  4. additionwas added to the residue
  5. extractionThe resulting aqueous phase was extracted with diethyl ether
  6. washthe organic extracts were washed with water and brine
  7. dry with materialbefore drying over anhydrous magnesium sulphate and evaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3e727cac35f640b383df5c84692b4630
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05116862

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