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

HRID 894986Notes

Reaction equation

HRID 894986 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 90.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 6,7-diacetoxychromone-3-carboxylic acid (18.4 g, 60 mmol), benzene (450 ml), thionyl chloride (8.6 g, 72 mmol) and N,N-dimethylformamide (3 ml) was refluxed for one hour and cooled to room temperature. After the addition of n-hexane (300 ml), the resulting precipitate was filtered off to give the desired compound (17.6 g).

Workup

  1. temperaturewas refluxed for one hour
  2. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-6f26a8ad38ab4f999b03caae304f7595
Source dataset
uspto-grants-1981_08
Patent number
US04285940

Reaction notes

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