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

HRID 895006Notes

Reaction equation

HRID 895006 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 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 collected to give the desired compound (17.6 g).

Workup

  1. temperaturewas refluxed for one hour
  2. customthe resulting precipitate was collected

Sources & evidence

ORD record
ord-651bf69362364c02ae22342ab104662e
Source dataset
uspto-grants-1981_08
Patent number
US04285941

Reaction notes

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