Acetone → HCID 10266436, compound

HRID 375007Notes

Reaction equation

HRID 375007 reaction equation
[C:1]([C:9]1[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.C(=O)([O-])[O-].[K+].[K+].Br[CH:31](C(OCC)=O)[C:32]([O:34]CC)=[O:33]>CN(C=O)C>[CH3:18][C:16]1[CH:17]=[C:9]2[C:10](=[CH:14][C:15]=1[CH3:19])[C:11](=[O:12])[O:13][C:31]([C:32]([OH:34])=[O:33])=[C:1]2[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 15214193HCID 15214193, compound

Product 1

HCID 10266436HCID 10266436, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-benzoyl-4,5-dimethylbenzoic acid (11.4 g), acetone (300 ml), DMF (10 ml), potassium carbonate (6.83 g) and diethyl bromomalonate (12.84 g) was stirred at room temperature for 60 hours. After the solvent was distilled off, ethyl acetate was added to the residue. This mixture was washed with water and then dried, after which the solvent was distilled off. To the residue were added acetic acid (180 ml) and hydrochloric acid (180 ml), followed by heating at 110° C. for 5 hours. The reaction mixture was concentrated, and water was added to the concentrate, followed by extraction with ethyl acetate. The extract was washed with water and then dried, after which the solvent was distilled off, to yield colorless crystals. The crystals were recrystallized from ethyl acetate-isopropyl ether to yield 6,7-dimethyl-4-phenylisocoumarin-3-carboxylic acid (≡6,7-dimethyl-1-oxo-4-phenyl-1H-2-benzopyran-3-carboxylic acid).

Workup

  1. distillationAfter the solvent was distilled off
  2. additionethyl acetate was added to the residue
  3. washThis mixture was washed with water
  4. customdried
  5. distillationafter which the solvent was distilled off
  6. additionTo the residue were added acetic acid (180 ml) and hydrochloric acid (180 ml)
  7. temperatureby heating at 110° C. for 5 hours
  8. concentrationThe reaction mixture was concentrated
  9. additionwater was added to the concentrate
  10. extractionfollowed by extraction with ethyl acetate
  11. washThe extract was washed with water
  12. customdried
  13. distillationafter which the solvent was distilled off
  14. customto yield colorless crystals
  15. customThe crystals were recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-44fb656ad679454e81803d866df432b9
Source dataset
uspto-grants-1996_01
Patent number
US05482967

Reaction notes

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