Hydrochloric Acid → Genipin

HRID 1492664Notes

Reaction equation

HRID 1492664 reaction equation
[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]

Participants

9

Reactant 6

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

Product 1

HCID 442424GenipinYield 73.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

First, 100 g of geniposide was dissolved in 650 ml 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.

Workup

  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

Sources & evidence

ORD record
ord-2c72108be9f44b31b6f3bd4237e9e0ad
Source dataset
uspto-grants-1994_12
Patent number
US05374653

Reaction notes

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