1-Propanone, 1-(2-hydroxyphenyl)-3-phenyl- → HCID 11558573, compound

HRID 498979Notes

Reaction equation

C[C@@H]1O[C@@H](O[C@H]2[C@H]([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[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O.C1C=CC(CCC(C2C=CC=CC=2O)=O)=CC=1>Cl>[OH:36][C:18]1[CH:17]=[C:16]([OH:15])[CH:21]=[C:20]([OH:22])[C:19]=1[CH:25]([OH:26])[CH2:24][CH2:23][C:27]1[CH:28]=[CH:29][C:30]([O:34][CH3:35])=[C:31]([OH:33])[CH:32]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Neohesperidin is a glycoside of dihydrochalcone. A total weight of 100 mg of neohesperidin was suspended in 10 ml of 1N HCl and heated at 80° C. for 2 hours. The hydrolyzed product (10) was cooled down and extracted with ethyl acetate (3×10 ml). The ethyl acetate layers were combined, evaporated to remove ethyl acetate and dissolved in 1-propanol (5 ml). Sodium borohydride (25 mg) was added to the propanol solution and stirred at room temperature for 2 hours. After the completion of the reaction, the mixture was separated on a pre-packed C18 column eluting with a MeOH/H2O gradient to provide 1-(2,4,6-trihydroxyphenyl)-3-(3′-hydroxy-4′-methoxyphenyl)-1-propanol (11).

Workup

extractionextracted with ethyl acetate (3×10 ml)
customevaporated
customto remove ethyl acetate
dissolutiondissolved in 1-propanol (5 ml)
additionSodium borohydride (25 mg) was added to the propanol solution
customAfter the completion of the reaction
customthe mixture was separated on a pre-packed C18 column
washeluting with a MeOH/H2O gradient

Sources & evidence

ORD record: ord-ec7c2000959f40388bf0ce38b2e60689
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767661B2

Reaction notes

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