Isoflavone → 3-Phenyl-2,3-dihydro-4H-1-benzopyran-4-one

HRID 2292123Notes

Reaction equation

HRID 2292123 reaction equation
[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:2]1>C(O)(=O)C.[Pd]>[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[CH:3]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:2]1

Participants

4

Reactant 1

HCID 72304Isoflavone

Product 1

HCID 1607673-Phenyl-2,3-dihydro-4H-1-benzopyran-4-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Isoflavone (3.00 g) was dissolved in acetic acid (100 ml), and the solution hydrogenated at 50°-60° and 10.4-13.8 atm using 10% w/v palladium or carbon catalyst. The solution was filtered and evaporated, and the residue chromatographed on alumina, eluting with toluene. The product thus obtained gave, on recrystallisation from petroleum ether, (60°-80°) isoflavanone, 0.90 g., m.pt 73°-76°.

Workup

  1. customhydrogenated at 50°-60°
  2. filtrationThe solution was filtered
  3. customevaporated
  4. customthe residue chromatographed on alumina
  5. washeluting with toluene
  6. customThe product thus obtained

Sources & evidence

ORD record
ord-cfc08dc7273e4acca11d397a90ffe462
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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