Hydrochloric Acid → Genipin

HRID 2210647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2210647
[CH3:1][O:2][C:3]([C:5]1[C@H:10]2[CH2:11][CH:12]=[C:13]([CH2:14][OH:15])[C@H:9]2[C@H:8]([O:16][C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[O:7][CH:6]=1)=[O:4].I([O-])(=O)(=O)=O.[Na+].B.[Na].Cl.S([O-])(O)=O.[Na+].[Cl-].[Na+]>O.CCOCC>[CH3:1][O:2][C:3]([C:5]1[C@H:10]2[CH2:11][CH:12]=[C:13]([CH2:14][OH:15])[C@H:9]2[C@H:8]([OH:16])[O:7][CH:6]=1)=[O:4]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 107848GeniposideHCID 23665763Sodium BisulfiteHCID 23667635Sodium periodateHCID 178418435HCID 178418435, Verbindung

Produkt 1

HCID 442424GenipinAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

First, 100 g of geniposide was dissolved in 650 mι of water. After 115 g of sodium periodate was added to the solution, the reaction mixture was stirred at room temperature for two hours. After 41 g of sodium boron hydride was further added, the reaction mixture was further stirred at room temperature for two hours. Subsequently, a 6N aqueous hydrochloric acid solution and ether were added, the reaction mixture was stirred at room temperature for four hours. After the addition of sodium hydrogen sulfite and sodium chloride, the reaction mixture was stirred to thereby separate an ether layer. After the ether layer was separated and dried, ether was distilled off, and a yellow solid was obtained. The solid was further recrystallized from methanol and ether to yield 43 g of genipin.

Aufarbeitung

  1. stirringthe reaction mixture was further stirred at room temperature for two hours
  2. stirringthe reaction mixture was stirred at room temperature for four hours
  3. stirringthe reaction mixture was stirred
  4. customto thereby separate an ether layer
  5. customAfter the ether layer was separated
  6. customdried
  7. distillationether was distilled off
  8. customa yellow solid was obtained
  9. customThe solid was further recrystallized from methanol and ether

Quellen und Nachweise

ORD-Eintrag
ord-9ad3ed8ffe7e40a7bb170027372d0d1b
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05459160

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