2,3-Dimethyl-1,3-butadiene → Dimethyl 4,5-dimethyl-1,4-cyclohexadiene-1,2-dicarboxylate

HRID 1186037

Reaktionsgleichung

Reaktionsgleichung von HRID 1186037
[CH3:1][C:2]([C:4]([CH3:6])=[CH2:5])=[CH2:3].[CH3:7][O:8][C:9](=[O:16])[C:10]#[C:11][C:12]([O:14][CH3:15])=[O:13]>C1C=CC=CC=1>[CH3:7][O:8][C:9]([C:10]1[CH2:5][C:4]([CH3:6])=[C:2]([CH3:3])[CH2:1][C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[O:16]

Komponenten

4

Edukt 2

HCID 105662,3-Dimethyl-1,3-butadieneHCID 12980Dimethyl acetylenedicarboxylate

Produkt 1

HCID 600973Dimethyl 4,5-dimethyl-1,4-cyclohexadiene-1,2-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

2,3-Dimethyl-buta-1,3-diene (2.0 g, 24.3 mmol) and but-2-ynedioic acid dimethyl ester in benzene (14 mL) were heated to reflux for 16 h. The resulting mixture was cooled and evaporated in vacuo to yield a solid, which was purified via flash column chromatography (EtOAc/heptane 9:1) to yield 4,5-dimethyl-cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester as a white solid.

Aufarbeitung

  1. temperatureto reflux for 16 h
  2. temperatureThe resulting mixture was cooled
  3. customevaporated in vacuo
  4. customto yield a solid, which
  5. customwas purified via flash column chromatography (EtOAc/heptane 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-4307b53bc2a749249ff6a351f85daebc
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673890B2

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