(+/-)-Naringenin → 2-[4-(Acetyloxy)phenyl]-4-oxo-3,4-dihydro-2H-1-benzopyran-5,7-diyl diacetate

HRID 1462962Notes

Reaction equation

HRID 1462962 reaction equation
[OH:1][C:2]1[CH:20]=[CH:19][C:5]([CH:6]2[CH2:15][C:14](=[O:16])[C:13]3[C:8](=[CH:9][C:10]([OH:18])=[CH:11][C:12]=3[OH:17])[O:7]2)=[CH:4][CH:3]=1.C(O[C:25](=[O:27])[CH3:26])(=O)C>S(=O)(=O)(O)O.O>[C:2]([O:1][C:2]1[CH:20]=[CH:19][C:5]([CH:6]2[CH2:15][C:14](=[O:16])[C:13]3[C:8](=[CH:9][C:10]([O:18][C:25](=[O:27])[CH3:26])=[CH:11][C:12]=3[O:17][C:6](=[O:7])[CH3:5])[O:7]2)=[CH:4][CH:3]=1)(=[O:1])[CH3:3]

Participants

5

Reactant 2

HCID 932(+/-)-NaringeninHCID 7918Acetic Anhydride

Product 1

HCID 143549842-[4-(Acetyloxy)phenyl]-4-oxo-3,4-dihydro-2H-1-benzopyran-5,7-diyl diacetate

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

4',5,7-Trihydroxyflavanone (10.5 g) was stirred with acetic anhydride (50 ml) and sulphuric acid (5 drops) for 2 hr at room temperature, then poured into iced water. The product was extracted into ether and the extracted washed with water, followed by sodium bicarbonate solution. 4',5,7-Triacetoxyflavanone was obtained on evaporation of the ether, and this was dissolved in a mixture of tetrahydrofuran (250 ml) and ethanol (250 ml). Sodium borohydride (1.2 g) was added over 5 min, and the solution stirred for 30 min. Further borohydride (1.8 g) was then added and stirring continued for a further 30 min. The solution was acidifed by cautious addition of glacial acetic acid (8 ml). The solvent was evaporated off and the residual oil extracted into chloroform, washed with water, dried and evaporated.

Workup

  1. extractionThe product was extracted into ether
  2. washthe extracted washed with water

Sources & evidence

ORD record
ord-9bfea1754da6485bbd83fc6425090299
Source dataset
uspto-grants-1984_07
Patent number
US04461907

Reaction notes

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