4-Oxo-4H-1-benzopyran-2-carbonyl chloride → 2-Benzoyl-4H-1-benzopyran-4-one

HRID 2292626Notes

Reaction equation

HRID 2292626 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[C:2]1[C:12](Cl)=[O:13].[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[C:12]([C:2]1[O:1][C:10]2[C:5]([C:4](=[O:11])[CH:3]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 787884-Oxo-4H-1-benzopyran-2-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 127520732-Benzoyl-4H-1-benzopyran-4-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Combine chromone-2-carboxylic acid chloride (2.0 g, 9.6 mmol) and aluminum chloride (3.84 g, 28.7 mmol) in benzene (70 mL). Heat at reflux for 4 hours. Pour the reaction mixture into ice-water (150 mL). Extract with dichloromethane twice. Dry the separated organic layers over MgSO4, filter, and evaporate in vacuo. Chromatograph on silica gel eluting with 15% ethyl acetate/hexane. Evaporate the product containing fractions to give the title compound as a solid.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 4 hours
  3. extractionExtract with dichloromethane twice
  4. dry with materialDry the separated organic layers over MgSO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customEvaporate the product
  8. additioncontaining fractions

Sources & evidence

ORD record
ord-3355e4999d794acdbd765d8725b5597a
Source dataset
uspto-grants-1997_11
Patent number
US05684017

Reaction notes

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