Carbon Dioxide → 6-Methylhepta-3,5-dien-2-one

HRID 363822

Reaktionsgleichung

Reaktionsgleichung von HRID 363822
[C:1]([O:7]C)(=O)[CH2:2][C:3]([CH3:5])=O.[CH3:9][C:10](O)(C#C)[CH3:11].[C:15](=O)=O>CCC(CC([O-])=O)=O.CCC(CC([O-])=O)=O.CCC(CC([O-])=O)=O.[Al+3].C1(=O)OC(C)CO1>[CH3:9][C:10](=[CH:5][CH:3]=[CH:2][C:1](=[O:7])[CH3:15])[CH3:11]

Komponenten

6

Edukt 3

HCID 280Carbon DioxideHCID 7757Methyl acetoacetateHCID 82582-Methyl-3-butyn-2-ol

Produkt 1

HCID 279716-Methylhepta-3,5-dien-2-oneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 18676716Aluminum tri(methyl acetylacetate)KatalysatorHCID 7924Propylene CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of 5.3 g of the aluminum tri(methyl acetylacetate) catalyst mentioned in Example 1 and 85 g of 1,2-propylene carbonate was heated to 170° C. and, at this temperature a mixture of 55 g (0.47 mol) of methyl acetoacetate and 43.7 g (0.52 mol) of 2-methyl-3-butyn-2-ol was metered in at a constant rate over the course of 4 h. After the addition was complete, the mixture was stirred at 170° C. for 30 min. During this time, CO2 was evolved and low boilers distilled out. The reaction mixture was subsequently cooled, and the 2-methyl-2,4-heptadien-6-one which was formed was distilled out under about 100 mbar. This resulted in 42 g of pure 2-methyl-2,4-heptadien-6-one, which corresponds to a yield of 72% of theory based on reacted 2-methyl-3-butyn-2-ol.

Aufarbeitung

  1. customwas metered in at a constant rate over the course of 4 h
  2. additionAfter the addition
  3. distillationlow boilers distilled out
  4. temperatureThe reaction mixture was subsequently cooled

Quellen und Nachweise

ORD-Eintrag
ord-4457941ebbf8475a829019b2152c533d
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05874635

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