Dimethylformamide → 6,7-Bis(acetyloxy)-2-methyl-4-oxo-4H-1-benzopyran-3-carboxylic acid

HRID 1981242Notes

Reaction equation

HRID 1981242 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7]([CH3:13])=[C:6]([C:14]([OH:16])=[O:15])[C:5]2=[O:17].CN(C)C=O.[C:23](OC(=O)C)(=[O:25])[CH3:24].[C:30](OCC)(=[O:32])[CH3:31]>N1C=CC=CC=1>[C:23]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:30](=[O:32])[CH3:31])[O:8][C:7]([CH3:13])=[C:6]([C:14]([OH:16])=[O:15])[C:5]2=[O:17])(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 8857Ethyl Acetate2×HCID 13377328HCID 13377328, compound

Product 1

HCID 134585256,7-Bis(acetyloxy)-2-methyl-4-oxo-4H-1-benzopyran-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 6,7-dihydroxy-2-methylchromone-3-carboxylic acid (2.24 g), dimethylformamide (30 ml), ethyl acetate (10 ml), pyridine (2.3 ml) and acetic anhydride (2.3 ml) was stirred at room temperature for 3 hours. Ethyl acetate (100 ml) was added to the reaction mixture, and the organic layer was washed successively with 6N-HCl and water, and thereafter dried over anhydrous magnesium sulfate. The solvent was evaporated and ethyl ether was added to the residue. The resulting solid was collected by filtration. It was washed with a 1:1 mixed solvent of ethyl acetate and ethyl ether and then dried, to obtain the desired product (1.93 g).

Workup

  1. washthe organic layer was washed successively with 6N-HCl and water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. additionethyl ether was added to the residue
  5. filtrationThe resulting solid was collected by filtration
  6. washIt was washed with a 1:1 mixed solvent of ethyl acetate and ethyl ether
  7. customdried

Sources & evidence

ORD record
ord-675d917e39ce42ae8b450e3dd944ac33
Source dataset
uspto-grants-1985_04
Patent number
US04513145

Reaction notes

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