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

HRID 67092Notes

Reaction equation

HRID 67092 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>CCCCCC>[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

6

Reactant 4

HCID 241BenzeneHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 122007746,7-Diacetoxychromone-3-carboxylic acid

Product 1

HCID 155748963-(Chlorocarbonyl)-4-oxo-4H-1-benzopyran-6,7-diyl diacetateYield 90.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 6,7-diacetoxychromone-3-carboxylic acid (18.4 g), benzene (450 ml), 8.6 g of thionyl chloride (8.6 g) and dimethylformamide (3 ml) was refluxed for one hour and then cooled to room temperature. To the reaction mixture was added hexane (300 ml) and the precipitate separated out was recovered by filtration. There was thus obtained the desired product (17.6 g).

Workup

  1. temperaturewas refluxed for one hour
  2. customthe precipitate separated out
  3. filtrationwas recovered by filtration

Sources & evidence

ORD record
ord-c846d4b9bbab4eebb83600bb1489d721
Source dataset
uspto-grants-1982_08
Patent number
US04344944

Reaction notes

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