Acetic Acid → 2-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-

HRID 1980618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1980618
C([O-])(=[O:3])C.[Na+].C(O)(=O)C.[CH3:10][C:11]1[O:15][C:14]([CH:16]=[CH:17][CH2:18][CH2:19]O)=[CH:13][CH:12]=1.[Cl-].[Na+]>O>[CH2:17]([C:16]1[C:14](=[O:15])[CH2:13][CH:12]([OH:3])[C:11]=1[CH3:10])[CH:18]=[CH2:19]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 517045Sodium AcetateHCID 704783345-Methyl-2-furylallylcarbinol

Produkt 1

HCID 110832-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-Ausbeute 219,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A buffer solution was prepared by dissolving sodium acetate (1.03 g) and Paion D-408 (polyoxyethylene alkyl phenyl ether; manufactured by Takemoto Yushi Inc.) (0.44 g) in water (200 ml) and adjusting the pH value to 6.0 with acetic acid. In a reaction vessel, 5-methyl-2-furylallylcarbinol (5 g) and the entire amount of the buffer solution as prepared above were charged, and the temperature was elevated up to 150° C. in 35 minutes while stirring. The mixture was stirred at the same temperature for 3.5 hours. After ice-cooling, sodium chloride (50 g) was added, and the mixture was extracted with methyl isobutyl ketone (100 ml) four times. The extract was concentrated at 60° C. under reduced pressure to remove methyl isobutyl ketone, whereby an oily substance (4.6 g) was obtained. The crude product was purified by column chromatography with silica gel (60 g) (developing solvent, ethyl acetate-n-hexane (1:2 by volume)) to obtain 2-allyl-3-methyl-4-hydroxy-2-cyclopentenone (4.2 g). Yield, 84%.

Aufarbeitung

  1. customA buffer solution was prepared
  2. additionabove were charged
  3. stirringThe mixture was stirred at the same temperature for 3.5 hours
  4. temperatureAfter ice-cooling
  5. extractionthe mixture was extracted with methyl isobutyl ketone (100 ml) four times
  6. concentrationThe extract was concentrated at 60° C. under reduced pressure
  7. customto remove methyl isobutyl ketone, whereby an oily substance (4.6 g)
  8. customwas obtained
  9. customThe crude product was purified by column chromatography with silica gel (60 g) (developing solvent, ethyl acetate-n-hexane (1:2 by volume))

Quellen und Nachweise

ORD-Eintrag
ord-4b7e38ede6874f5e84f6cdb7e994f323
Quelldatensatz
uspto-grants-1985_04
Patentnummer
US04510329

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