Hydrochloric Acid → Genipin

HRID 2210647Notes

Reaction equation

HRID 2210647 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 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.

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-9ad3ed8ffe7e40a7bb170027372d0d1b
Source dataset
uspto-grants-1995_10
Patent number
US05459160

Reaction notes

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