Water → Xenognosin B

HRID 2360112Notes

Reaction equation

HRID 2360112 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][C:16]([OH:22])=[CH:17][CH:18]=2)[O:13][CH:12]=1.[Al+3].[Cl-].[Cl-].[Cl-].O>CC#N>[OH:22][C:16]1[CH:15]=[C:14]2[C:19]([C:20](=[O:21])[C:11]([C:4]3[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=3[OH:2])=[CH:12][O:13]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5781145HCID 5781145, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5280551Xenognosin BYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 3-(2,4-dimethoxy-phenyl)-7-hydroxy-chromen-4-one (2 gm, 6.7 mmol) was dissolved in CH3CN (25 ml) and AlCl3 (2.6 gm, 20 mmol) was added to the solution at 0° C. The reaction was then refluxed for 10 hours. The mixture was cooled and then poured ice-cooled water. The precipitated solid were filtered, washed with water and purified by silica gel column chromatography using chloroform-methanol as the eluent to give 7-hydroxy-3-(2-hydroxy-4-methoxy-phenyl)-chromen-4-one (0.95 gm, 50%) as white solid.

Workup

  1. temperatureThe reaction was then refluxed for 10 hours
  2. temperatureThe mixture was cooled
  3. filtrationThe precipitated solid were filtered
  4. washwashed with water
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-8be1ce95019448cea9f2b6aa9630c247
Source dataset
uspto-grants-2014_04
Patent number
US08686028B2

Reaction notes

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