Neohesperidin → Neohesperidin dihydrochalcone

HRID 268162Notes

Reaction equation

HRID 268162 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([O:15][C:16]3[CH:17]=[C:18]([OH:36])[C:19]4[C:25](=[O:26])[CH2:24][C@@H:23]([C:27]5[CH:28]=[CH:29][C:30]([O:34][CH3:35])=[C:31]([OH:33])[CH:32]=5)[O:22][C:20]=4[CH:21]=3)[O:13][C@H:12]([CH2:37][OH:38])[C@@H:11]([OH:39])[C@@H:10]2[OH:40])[C@H:5]([OH:41])[C@H:4]([OH:42])[C@H:3]1[OH:43].[H][H]>[OH-].[Na+].[Ni]>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([O:15][C:16]3[CH:17]=[C:18]([OH:36])[C:19]([C:25]([CH2:24][CH2:23][C:27]4[CH:28]=[CH:29][C:30]([O:34][CH3:35])=[C:31]([OH:33])[CH:32]=4)=[O:26])=[C:20]([OH:22])[CH:21]=3)[O:13][C@H:12]([CH2:37][OH:38])[C@@H:11]([OH:39])[C@@H:10]2[OH:40])[C@H:5]([OH:41])[C@H:4]([OH:42])[C@H:3]1[OH:43]

Participants

5

Reactant 2

HCID 442439NeohesperidinHCID 178418361HCID 178418361, compound

Product 1

HCID 30231Neohesperidin dihydrochalconeYield 95%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 14798Sodium HydroxideSolvent

Procedure

18.9 g (0.030 mol) of neohesperidin are dissolved in 90 ml of 2-N sodium hydroxide and treated with 1.2 g of Raney-nickel. The mixture is hydrogenated under normal pressure for 15 hours. The hydrogen uptake corresponds to 30 mmol. The solution is filtered and adjusted to pH 6 with 36 ml of 5-N hydrochloric acid while cooling with ice and stirring. The resulting clear yellow solution is left in a refrigerator for 48 hours and then filtered under suction. The white residue is washed with cold water and dried overnight in a high vacuum. There are obtained 17.4 g (95% yield) of neohesperidin dihydrochalcone of melting point 150°C.

Workup

  1. filtrationThe solution is filtered
  2. temperaturewhile cooling with ice
  3. waitThe resulting clear yellow solution is left in a refrigerator for 48 hours
  4. filtrationfiltered under suction
  5. washThe white residue is washed with cold water
  6. customdried overnight in a high vacuum

Sources & evidence

ORD record
ord-41c977cd51e04c94b1a761f200df09b2
Source dataset
uspto-grants-1976_03
Patent number
US03947405

Reaction notes

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