HCID 18768827, compound → HCID 18768835, compound

HRID 480096Notes

Reaction equation

HRID 480096 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][C:7]=1[C:15]([O:17]C)=[O:16]>[OH-].[K+]>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][C:7]=1[C:15]([OH:17])=[O:16]

Participants

3

Reactant 1

HCID 18768827HCID 18768827, compound

Product 1

HCID 18768835HCID 18768835, compound

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

4-(2-furyl)-3-(methoxycarbonyl)phenyl-1-ethanone (3.85 g, 15.78 mmol) was heated to reflux in 20% methanolic potassium hydroxide (200 ml) for 15 minutes. Most of the methanol was removed under reduced pressure. The residue was dissolved in water and washed with methylene chloride. The aqueous solution was acidified to pH 1 with 12N hydrochloric acid and the product extracted with ethyl acetate. The organic solution was washed with water and brine, dried over sodium sulfate, filtered, and evaporated. The crude product was recrystallized from toluene to give the title compound.

Workup

  1. customMost of the methanol was removed under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. washwashed with methylene chloride
  4. extractionthe product extracted with ethyl acetate
  5. washThe organic solution was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was recrystallized from toluene

Sources & evidence

ORD record
ord-37a3a70958224ce0ae8c83289ae19a8a
Source dataset
uspto-grants-2003_11
Patent number
US06649636B1

Reaction notes

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