Phlorizin → 3,5-Dioxohexanoic acid

HRID 1005646

Reaktionsgleichung

Reaktionsgleichung von HRID 1005646
C1C(CCC(C2C(O)=CC(O)=CC=2O[C@@H:18]2O[C@H:22]([CH2:24][OH:25])[C@@H:21]([OH:26])[C@H:20](O)[C@H:19]2[OH:28])=O)=CC=C(O)C=1.C([O-])(=[O:34])C.[Na+]>C(OC(=O)C)(=O)C>[CH3:18][C:19]([CH2:20][C:21]([CH2:22][C:24]([OH:34])=[O:25])=[O:26])=[O:28]

Komponenten

4

Edukt 2

HCID 6072PhlorizinHCID 517045Sodium Acetate

Produkt 1

HCID 54598443,5-Dioxohexanoic acidAusbeute 181,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

1 g of phlorizin, 10 mL of acetic anhydride and 0.82 g (0.01 mol) of sodium acetate were reacted at 100° C. for 6 hrs. The reaction mixture was cooled and the triacetate derivative of phlorizin precipitated from the solution in the form of a crystalline solid. The crystalline solid was separated by filtration, dissolved in 50 mL of hot methanol, and re-crystallized twice from hot methanol. The reaction yielded 0.6 g of the triacetate. 0.3 g of the triacetate and 1.3 mL of 0.2 M sulfuric acid in 100 mL of water were heated to reflux and refluxed for 3 hrs. The reaction mixture was cooled yielding the triacetate of phloretin in about a 45% yield.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customthe triacetate derivative of phlorizin precipitated from the solution in the form of a crystalline solid
  3. customThe crystalline solid was separated by filtration
  4. dissolutiondissolved in 50 mL of hot methanol
  5. customre-crystallized twice from hot methanol

Quellen und Nachweise

ORD-Eintrag
ord-5589b4699ed64c648ccb0c682501a054
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787528B2

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