Potassium Hydroxide → 3,3-Dimethylpent-4-enoic acid

HRID 1683332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683332
[CH3:1][C:2]([CH3:10])([CH:8]=[CH2:9])[CH2:3][C:4]([O:6]C)=[O:5].[OH-].[K+]>C(O)C>[CH3:1][C:2]([CH3:10])([CH:8]=[CH2:9])[CH2:3][C:4]([OH:6])=[O:5]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 114129Methyl 3,3-dimethyl-4-pentenoate

Produkt 1

HCID 106304993,3-Dimethylpent-4-enoic acidAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 3,3-dimethylpent-4-enoate (0.5 mole) in 500 ml of ethanol (95% grade) was added potassium hydroxide (1 mole). The solution was refluxed for 1.5 hours. After cooling down to room temperature, the solution was concentrated to 200 ml on a rotary evaporator, and acidified by the addition of 5N H2SO4 solution. The product was isolated by extraction with diethyl ether (3×200 mls). After removal of the solvent, the crude product was distilled under reduced pressure to yield the pure acid (77%) b.p. 78°-80° C. (1.5 mmHg). 1H NMR (CDCl3) δ10.60 (1H, broad s), 5.90 (1H, dd, J 10.3, 17.6 Hz), 5.00 (1H, dd, J 17.6 Hz, J 1.3 Hz), 4.97 (1H, dd, J 10.3 Hz, J 1.3 Hz), 2.35 (2H, s), and 1.20 (6H, s).

Aufarbeitung

  1. temperatureThe solution was refluxed for 1.5 hours
  2. concentrationthe solution was concentrated to 200 ml on a rotary evaporator
  3. additionacidified by the addition of 5N H2SO4 solution
  4. customThe product was isolated by extraction with diethyl ether (3×200 mls)
  5. customAfter removal of the solvent
  6. distillationthe crude product was distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-66ae219a60f944459da5f279e8c7c131
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05637718

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