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

HRID 2292124Notes

Reaction equation

HRID 2292124 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:2]1>C(O)(=O)C.Cl.[Zn]>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:2]1

Participants

5

Reactant 1

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

Product 1

HCID 500472Isoflavan

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

Isoflavanone (0.90 g) was dissolved in a mixture of acetic acid (15 ml) and concentrated hydrochloric acid (1.5 ml). and the solution added to zinc amalgam prepared from zinc powder (2.5 g) and mercuric chloride (0.25 g). The mixture was stirred for 45 min., then allowed to stand at room temperature for 18 hrs. The mixture was filtered and the filtrate diluted with water. The precipitated oil was extracted into toluene and the extract washed with saturated sodium hydrogen bicarbonate solution, dried, and evaporated. The residue was chromatographed on alumina, eluting with petroleum ether, (60°-80°) to give, on evaporation of the eluate, pure isoflavan, 0.23 g., m.pt. 54°-56°.

Workup

  1. waitto stand at room temperature for 18 hrs
  2. filtrationThe mixture was filtered
  3. additionthe filtrate diluted with water
  4. extractionThe precipitated oil was extracted into toluene
  5. washthe extract washed with saturated sodium hydrogen bicarbonate solution
  6. customdried
  7. customevaporated
  8. customThe residue was chromatographed on alumina
  9. washeluting with petroleum ether, (60°-80°)

Sources & evidence

ORD record
ord-9692c5fc4f5f4828b6f8ffba9e4914a1
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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