Potassium Carbonate → HCID 22664926, compound

HRID 392603Notes

Reaction equation

HRID 392603 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-glycidylcoumarin was prepared in a reaction flask equipped with a reflux condenser containing 16.2 g 7-hydroxycournarin, 15.8 g epibromohydrin, 13.8 g potassium carbonate and 270 mL acetone. The reaction solution was boiled and refluxed overnight, cooled, treated with 100 mL 5% NaOH aqueous solution, and extracted three times with 80 mL 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 hr. White crystals formed and were collected by filtering and dried to a white powder. Yield: 290 mg; melting point: 110-112° C.; Rf=0.6 (8% v/v ethyl acetate/CHCl3).

Workup

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

Sources & evidence

ORD record
ord-21d4ac94c08b4614b858e4c36256401f
Source dataset
uspto-grants-2004_10
Patent number
US06800768B1

Reaction notes

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