Water → 7-Hydroxy-2-methyl-3-phenyl-4H-chromen-4-one

HRID 1296866Notes

Reaction equation

HRID 1296866 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:17])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:18](OC(=O)C)(=O)[CH3:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[OH:8][C:6]1[CH:7]=[C:2]2[C:3]([C:9](=[O:17])[C:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[C:18]([CH3:19])[O:1]2)=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 138005Benzyl 2,4-dihydroxyphenyl ketone

Product 1

HCID 53809767-Hydroxy-2-methyl-3-phenyl-4H-chromen-4-oneYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2,4-Dihydroxy-phenyl)-2-phenyl-ethanone (0.5 g, 3.2 mmol) was refluxed in anhydrous DMF with acetic anhydride (1.5 ml), and anhydrous potassium carbonate (1.4 g 10.1 mmol) for 3 hrs. The solution was then poured into water and the precipitate filtered to give 7-hydroxy-2-methyl-3-phenyl-chromen-4-one as white solid (0.62 g, 66%); Rf 0.75 cf SM 0.9 ethyl acetate/hexane (75/25).

Workup

  1. filtrationthe precipitate filtered

Sources & evidence

ORD record
ord-d7f1d1f7acbe4b57ab9eaf42840fed35
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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