Potassium Carbonate → HCID 22664926, compound

HRID 612967Notes

Reaction equation

HRID 612967 reaction equation
O[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[CH2:13]([CH:15]1[O:17][CH2:16]1)Br.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CCCCCC.CC(C)=O.CCCCCC.CC(C)=O>[CH2:13]([C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1)[CH:15]1[O:17][CH2:16]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 18430EpibromohydrinHCID 5281426Umbelliferone

Product 1

HCID 22664926HCID 22664926, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 8058HexaneSolventHCID 21880519Acetone hexaneSolvent

Procedure

The intermediate 7-glycidyl coumarin was prepared in a reaction flask equipped with a reflux condenser containing 16.2 g of 7-hydroxycoumarin, 15.8 g of epibromohydrin, 13.8 g of potassium carbonate and 270 ml of acetone ("reaction solution"). The reaction solution was boiled and refluxed overnight, cooled, treated with 100 ml of 5% NaOH aqueous solution, and extracted three times with 80 ml of methylene chloride. After evaporating the solvent a crude yellow solid was obtained. The crude solid (1.5 g) was dissolved in a solution of 30 ml hexane and 20 ml acetone at 50° C. The hexane/acetone solution was then cooled at 0° C. for 2 to 3 hours. White crystals formed and were collected by filtering and dried to a white powder. 290 mg of white powder was obtained. The melting point of this new compound (7-glycidyl coumarin) was 110-112° C. Thin layer chromatography (TLC) was done in 8% (v/v ethyl acetate/CHCl3 ; the Rf value of the 7-glycidyl coumarin was 0.6.

Workup

  1. customequipped with a reflux condenser
  2. temperaturerefluxed overnight
  3. temperaturecooled
  4. extractionextracted three times with 80 ml of methylene chloride
  5. customAfter evaporating the solvent a crude yellow solid
  6. customwas obtained
  7. customWhite crystals formed
  8. customwere collected
  9. filtrationby filtering
  10. customdried to a white powder

Sources & evidence

ORD record
ord-8f4d12fd046c434c8ef7065d01cd4166
Source dataset
uspto-grants-1999_12
Patent number
US06005093

Reaction notes

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