Hydrogen Peroxide → 3-Hydroxy-7-iodo-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one

HRID 1819533Notes

Reaction equation

HRID 1819533 reaction equation
[OH:1][C:2]1[CH:23]=[C:22]([I:24])[CH:21]=[CH:20][C:3]=1[C:4](=[O:19])[CH:5]=[CH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1.[OH-:25].[Na+].OO>CO>[OH:25][C:5]1[C:4](=[O:19])[C:3]2[C:2](=[CH:23][C:22]([I:24])=[CH:21][CH:20]=2)[O:1][C:6]=1[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 688868382'-Hydroxy-4'-iodo-3,4,5-trimethoxy-chalcone

Product 1

HCID 578873343-Hydroxy-7-iodo-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 32 (0.165 g, 0.4 mmol) in methanol (4.4 ml) and 16% aqueous sodium hydroxide solution (0.6 ml, 2.4 mmol, 6.4 egu) at 0° C. was added 15% aqueous hydrogen peroxide (0.6 ml, 2.6 mmol, 7.1 equ) dropwise. The solution was stirred at 0° C. for ten minutes then sealed and placed in a refrigerator for 24 hours. The reaction was then filtered and then collected solid separated between 1N HCl and dichloromethane. The organic layer was then dried (MgSO4) and concentrated to give 3-hydroxy-7-iodo-2-(3,4,5-trimethoxyphenyl)-chromen-4-one as a yellow solid. Meanwhile filtrate was acidified (1N HCl) and the precipitated solid, 3-hydroxy-7-iodo-2-(3,4,5-trimethoxyphenyl)-chromen-4-one, collected. (Total yield 0.130 g, 76%).

Workup

  1. customthen sealed
  2. filtrationThe reaction was then filtered
  3. customcollected solid
  4. customseparated between 1N HCl and dichloromethane
  5. dry with materialThe organic layer was then dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bf2be6c31ae74628a85928e24a16bd3b
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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