Sulfuric Acid → Diacetone-D-glucose

HRID 843209

Reaktionsgleichung

Reaktionsgleichung von HRID 843209
S(=O)(=O)(O)O.[OH:6][C@H:7]1[O:15][C@H:14]([CH2:16][OH:17])[C@@H:12]([OH:13])[C@H:10]([OH:11])[C@H:8]1[OH:9].[OH-].[Na+]>CC(C)=O>[CH3:7][C:8]1([CH3:10])[O:13][C@@H:12]([C@H:14]2[O:15][C@@H:7]3[O:6][C:14]([CH3:16])([CH3:12])[O:9][C@@H:8]3[C@H:16]2[OH:17])[CH2:10][O:11]1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 79025Alpha-D-Glucose

Produkt 1

HCID 7067560Diacetone-D-glucoseAusbeute 112,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Sulfuric acid (40 ml) is added dropwise to a solution of α-D-glucose (41) (50 g, 0,28 mol) in acetone (1 l) at 0° C. The reaction mixture is stirred for 24 h and then it is neutralized using sodium hydroxide (6 M). The acetone is evaporated and the aqueous layer is extracted with chloroform (X2). The chloroform is dried (MgSO4) filtered and evaporated. Crystallization from cyclohexane yielded the di-isopropylidene glucose (42) (41 g, 57%).

Aufarbeitung

  1. customThe acetone is evaporated
  2. extractionthe aqueous layer is extracted with chloroform (X2)
  3. dry with materialThe chloroform is dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customCrystallization from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-80b91a09cd0a4ad6b1d6e94c624dd2c4
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376657B1

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