Benzene → 3-(Chlorocarbonyl)-4-oxo-4H-1-benzopyran-6,7-diyl diacetate

HRID 894981Notes

Reaction equation

HRID 894981 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][C:16](=[O:18])[CH3:17])[O:11][CH:10]=[C:9]([C:19](O)=[O:20])[C:8]2=[O:22])(=[O:3])[CH3:2].C1C=CC=CC=1.S(Cl)([Cl:31])=O>CN(C)C=O>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][C:16](=[O:18])[CH3:17])[O:11][CH:10]=[C:9]([C:19]([Cl:31])=[O:20])[C:8]2=[O:22])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 122007746,7-Diacetoxychromone-3-carboxylic acid

Product 1

HCID 155748963-(Chlorocarbonyl)-4-oxo-4H-1-benzopyran-6,7-diyl diacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6,7-Diacetoxychromone-3-carboxylic acid (918 mg, 3 mmol), benzene (20 ml), thionyl chloride (260 μl, 3.6 mmol) and N,N-dimethylformamide (0.2 ml) was refluxed for 2 hours and the solvent was removed. Benzene (5 ml) was added and then evaporated. This was repeated twice to remove traces of thionyl chloride. The residual solid was collected to afford the desired compound.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customthe solvent was removed
  3. additionBenzene (5 ml) was added
  4. customevaporated
  5. customto remove traces of thionyl chloride
  6. customThe residual solid was collected

Sources & evidence

ORD record
ord-143a0ece9ee9449c95084a3ffd3f5fab
Source dataset
uspto-grants-1981_08
Patent number
US04285939

Reaction notes

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