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

HRID 895008Notes

Reaction equation

HRID 895008 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 chloride

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), dimethylformamide (0.1 ml) and benzene (300 ml) was refluxed for 1.5 hours. After the addition of thionyl chloride (2.6 ml) was dimethylformamide (0.1 ml), the mixture was refluxed for a further one hour and evaporated to dryness. The residue was triturated with n-hexane to give the desired compound (9.3 g).

Workup

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

Sources & evidence

ORD record
ord-acfc866a4caa423ab0dafd12770d537f
Source dataset
uspto-grants-1981_08
Patent number
US04285941

Reaction notes

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