Water → 7-hydroxy-3-(4-methoxyphenyl)-2-methyl-4H-chromen-4-one

HRID 646452Notes

Reaction equation

HRID 646452 reaction equation
[C:1](OC(=O)C)(=O)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[OH:14][C:15]1[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:16]=1[C:22](=[O:32])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1.O>CN(C=O)C>[OH:21][C:19]1[CH:20]=[C:15]2[C:16]([C:22](=[O:32])[C:23]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)=[C:1]([CH3:2])[O:14]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 259632Ononetin

Product 1

HCID 54002317-hydroxy-3-(4-methoxyphenyl)-2-methyl-4H-chromen-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

Acetic anhydride (3 ml, 30 mmol) was added to a suspension of potassium carbonate (4.0 g, 29 mmol) and 1-(2,4-dihydroxy-phenyl)-2-(4-methoxy-phenyl)-ethanone (1.95 g, 7.5 mmol) in DMF (10 ml), and the resulting suspension heated at 115° C. for ˜90 mins. The mixture was allowed to cool and poured into water (200 ml), to give an off-white precipitate. The solids were removed by filtration and washed with water (100 ml) and diethyl ether (2×40 ml), to give 7-hydroxy-3-(4-methoxy-phenyl)-2-methyl-chromen-4-one as an off-white powder, dried in vacuo, (1.65 g)

Workup

  1. temperatureto cool
  2. customto give an off-white precipitate
  3. customThe solids were removed by filtration
  4. washwashed with water (100 ml) and diethyl ether (2×40 ml)

Sources & evidence

ORD record
ord-72feae3bb6644cdfacc54a821b41fa18
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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