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

HRID 67093Notes

Reaction equation

HRID 67093 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), thionyl chloride (2.6 ml), dimethylformamide (0.1 ml) and benzene (300 ml) was refluxed for one and half hours, and there were further added thionyl chloride (2.6 ml) and dimethyl formamide (0.1 ml). The whole was then refluxed for further one hour. Then the solvent was removed therefrom by distillation, and the residue was triturated with n-bexane. The solid matter thus obtained was collected by filtration. There was thus obtained the desired product (9.3 g).

Workup

  1. temperaturewas refluxed for one and half hours, and there
  2. temperatureThe whole was then refluxed for further one hour
  3. customThen the solvent was removed
  4. distillationby distillation
  5. customthe residue was triturated with n-bexane
  6. customThe solid matter thus obtained
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-ff0bd971812e41ecbadebac28b56bb55
Source dataset
uspto-grants-1982_08
Patent number
US04344944

Reaction notes

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