Acetic Anhydride → 3-(4-methoxy-phenyl)-2,8-dimethyl-4H-chromene-4,7-diol

HRID 1296947

Reaction equation

HRID 1296947 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].[C:27](OC(=O)C)(=O)[CH3:28]>CN(C=O)C.O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[CH:10]([OH:20])[C:3]3[C:2](=[C:7]([CH3:8])[C:6]([OH:9])=[CH:5][CH:4]=3)[O:1][C:27]=2[CH3:28])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 155208501-(2,4-Dihydroxy-3-methylphenyl)-2-(4-methoxyphenyl)ethanone

Product 1

HCID 589136083-(4-methoxy-phenyl)-2,8-dimethyl-4H-chromene-4,7-diol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2,4-dihydroxy-3-methyl-phenyl)-2-(4-methoxy-phenyl)-ethanone (1 eq) in anhydrous DMF was added K2CO3 (3 eq). Acetic anhydride (3 eq) was added dropwise to the solution, which was then refluxed, under nitrogen whilst stirring for 5 h. The solution was taken up in water and extracted using ethyl acetate, dried over MgSO4 and concentrated in vacuo to give 3-(4-methoxy-phenyl)-2,8-dimethyl-4H-chromene-4,7-diol as a yellow solid.

Workup

  1. temperaturewas then refluxed, under nitrogen
  2. extractionextracted
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e2ee292ce68441d906dd3caa09e726a
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Linked notes

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