Benzene → 7,8-Diacetoxychromone-3-carbonyl chloride

HRID 894988Notes

Reaction equation

HRID 894988 reaction equation
[C:1]([O:4][C:5]1[C:14]([O:15][C:16](=[O:18])[CH3:17])=[C:13]2[C:8]([C:9](=[O:22])[C:10]([C:19](O)=[O:20])=[CH:11][O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].S(Cl)([Cl:25])=O.C1C=CC=CC=1>CN(C)C=O>[C:1]([O:4][C:5]1[C:14]([O:15][C:16](=[O:18])[CH3:17])=[C:13]2[C:8]([C:9](=[O:22])[C:10]([C:19]([Cl:25])=[O:20])=[CH:11][O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 241BenzeneHCID 24386Thionyl Chloride2×HCID 127658457,8-Diacetoxychromone-3-carboxylic acid

Product 1

HCID 541479727,8-Diacetoxychromone-3-carbonyl chlorideYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 7,8-diacetoxychromone-3-carboxylic acid (9.5 g, 31 mmol), thionyl chloride (2.6 ml), N,N-dimethylformamide (0.1 ml) and benzene (300 ml) was refluxed for 1.5 hours. After the addition of thionyl chloride (2.6 ml) and N,N-dimethylformamide (0.1 ml), the mixture was refluxed for a further hour and evaporated to dryness. The residue was triturated with n-hexane to afford the desired compound (9.3 g, 92.6%).

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. temperaturethe mixture was refluxed for a further hour
  3. customevaporated to dryness
  4. customThe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-141be3f9c7f14b2cbf2b4e3b69c4e146
Source dataset
uspto-grants-1981_08
Patent number
US04285940

Reaction notes

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