3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one → HCID 70181280, compound

HRID 1077675Notes

Reaction equation

HRID 1077675 reaction equation
[OH:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH2:7][C:8]([C:10]2[C:11](=[CH:13][C:14](=[CH:16][C:17]=2[OH:18])[OH:15])[OH:12])=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+].C(OCC)(=O)C>CO.O>[OH:1][CH:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]([C:10]2[C:17](=[CH:16][C:14](=[CH:13][C:11]=2[OH:12])[OH:15])[OH:18])=[O:9])=[CH:19][CH2:20]1

Participants

6

Reactant 3

HCID 47883-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-oneHCID 8857Ethyl AcetateHCID 4311764Sodium borohydride

Product 1

HCID 70181280HCID 70181280, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Phloretin (25 mg) is dissolved in the minimum amount of methanol, diluted with water (3 ml) and treated with a slight excess of NaBH4. After 5 minutes the solution is carefully acidified, with ethyl acetate. The Organic phase is dried over Na2SO4 and evaporated to dryness to give 17 mg of dihydrophloretin as white powder, homogeneous on TLC analysis (silica gel, CHCl3 /MeOH/H2O 70:28:2).

Workup

  1. dry with materialThe Organic phase is dried over Na2SO4
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-e6a356067c3c4397b72f113997f80cc2
Source dataset
uspto-grants-1996_08
Patent number
US05545399

Reaction notes

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