Hydrochloric Acid → HCID 57887316, compound

HRID 1819541Notes

Reaction equation

HRID 1819541 reaction equation
[OH:1][C:2]1[CH:29]=[C:28]([I:30])[CH:27]=[CH:26][C:3]=1[C:4](=[O:25])[CH:5]=[CH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([O:23][CH3:24])[CH:8]=1.[OH-:31].[Na+].OO.Cl>CO>[OH:31][C:5]1[C:4](=[O:25])[C:3]2[C:2](=[CH:29][C:28]([I:30])=[CH:27][CH:26]=2)[O:1][C:6]=1[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([O:23][CH3:24])[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 68602872HCID 68602872, compound

Product 1

HCID 57887316HCID 57887316, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 33 (0.85 g, 1.6 mmol) in methanol (17 ml) and 16% aqueous sodium hydroxide solution (2.2 ml, 8.8 mmol, 5.3 equ) at 0° C. was added 15% aqueous hydrogen peroxide (2.2 ml, 9.7 mmol, 5.9 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 acidified (1N HCl) and extracted with dichloromethane (2×). The organic layer was then dried (MgSO4) and concentrated to give a dark yellow foam. This was triturated with ethanol to give 3-hydroxy-7-iodo-(4-benzyloxy-3,5-dimethoxyphenyl)-chromen-4-one (0.84 g, 96%) as a yellow solid.

Workup

  1. customthen sealed
  2. extractionextracted with dichloromethane (2×)
  3. dry with materialThe organic layer was then dried (MgSO4)
  4. concentrationconcentrated
  5. customto give a dark yellow foam
  6. customThis was triturated with ethanol

Sources & evidence

ORD record
ord-6f7d5581efe640b99866f14ebc1e6158
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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