Water → Trans 4-(5-methyl-2-furyl)-4-oxo-2-butenoic Acid

HRID 1194390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1194390
[C:1]([C:4]1[O:5][C:6]([CH3:9])=[CH:7][CH:8]=1)(=[O:3])[CH3:2].O.[C:11]([O:14]CC)(=[O:13])[CH3:12]>>[CH3:9][C:6]1[O:5][C:4]([C:1](=[O:3])/[CH:2]=[CH:12]/[C:11]([OH:14])=[O:13])=[CH:8][CH:7]=1

Komponenten

4

Edukt 3

HCID 962Water2×HCID 8857Ethyl AcetateHCID 145142-Acetyl-5-Methylfuran

Produkt 1

HCID 13565866Trans 4-(5-methyl-2-furyl)-4-oxo-2-butenoic Acid

Versuchsvorschrift

10 g of 2-acetyl 5-methyl furan (J. Am. Chem. Soc., 72 3695 (1950)), 7.4 g monohydrated glyoxylic acid and 5 cm3 water are heated to 120°-130° C. for 5 hours, while eliminating the water formed in the course of the reaction. After cooling, 60 cm3 ethyl acetate are added and extracted with a solution of sodium carbonate. The aqueous phase is acidified, extracted with ethyl acetate, dried, and concentrated to dryness. The residue is chromtographed on silica, then, the product is recrystallized in ethyl acetate. 2.2 g of the expected product are obtained. MP=159°-162° C.

Aufarbeitung

  1. customformed in the course of the reaction
  2. temperatureAfter cooling
  3. extractionextracted with a solution of sodium carbonate
  4. extractionextracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated to dryness
  7. customthe product is recrystallized in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d1f3c32ddce24802ab7cac12c2503e05
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04814348

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