반응 #355345

ord-d219e114a11d41cdabd448215e825d8e

반응 방정식

COc1ccc([C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)cc3O2)cc1O
neohesperidin
[H][H]
hydrogen
→
COc1ccc(CCC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)cc2O)cc1O
neohesperidin dihydrochalcone
수율 95.0%

반응물

COc1ccc([C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)cc3O2)cc1O
neohesperidin
[H][H]
hydrogen

시약

[Ni]
Raney-nickel

용매

—
2-N
[Na+].[OH-]
sodium hydroxide

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    여과The solution is filtered
  2. 2
    온도while cooling with ice
  3. 3
    workup.WAITThe clear yellow solution is left in a refrigerator for 48 hours
  4. 4
    여과filtered under suction
  5. 5
    세척The white residue is washed with cold water
  6. 6
    기타dried overnight in a high vacuum

실험 절차

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 for 15 hours under normal pressure. 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 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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US03947405uspto-grants-1976_03