Acetic Acid → 3-Formylbut-2-enyl acetate

HRID 129977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129977
[C:1]1([CH3:7])[CH:6]=[CH:5]C=C[CH:2]=1.[C:8]([OH:11])(=[O:10])[CH3:9].[OH2:12]>>[C:8]([O:11][CH2:5][CH:6]=[C:1]([CH3:7])[CH:2]=[O:12])(=[O:10])[CH3:9]

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 962WaterHCID 1140Toluene

Produkt 1

HCID 846993-Formylbut-2-enyl acetateAusbeute 74 %

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

1-Acetoxy-4-chloro-3-methyl-2-butene (7.8 g) was added to a suspension of hexamine (6.7 g) and acetonitrile (47 ml), and the mixture was stirred at room temperature for 16 hours. The precipitated crystals were separated by filtration to give crystals (12.5 g) of a quaternary ammonium salt. This salt (7.9 g) was dissolved in water (50 ml), and toluene (100 ml) was added. With stirring at 75° C., acetic acid (1.5 g per addition) was added 30 minutes, 1 hour and 2 hours after the beginning of the reaction. The reaction was stopped 6 hours after the beginning of the reaction. The toluene layer was separated and concentrated, and the resulting residue was purified by column chromatography on silica gel to give 4-acetoxy-2-methyl-2-buten-1-al (2.6 g, 74%).

Aufarbeitung

  1. customafter the beginning of the reaction
  2. customafter the beginning of the reaction
  3. customThe toluene layer was separated
  4. concentrationconcentrated
  5. customthe resulting residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e31a3fa858994b21a56ab6cd0d618236
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05471004

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