Acetone → HCID 10266436, compound

HRID 260450Notes

Reaction equation

HRID 260450 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 for 60 hours at room temperature. The solvent was distilled off. To the residue was added ethyl acetate. This mixture was washed with water and dried (Na2SO4), then the solvent was distilled off. To the residue were added acetic acid (180 ml) and hydrochloric acid (180 ml), and the mixture was heated for 5 hours at 110° C. The reaction mixture was concentrated, to which was added water, followed by extraction with ethyl acetate. The extract was washed with water, and dried (Na2SO4), then the solvent was distilled off to leave colorless crystals. Recrystallization from ethyl acetate-isopropyl ether to give 6,7-dimethyl-4-phenylisocumarin-3-carboxylic acid, m.p.265°-268° C.

Workup

  1. distillationThe solvent was distilled off
  2. additionTo the residue was added ethyl acetate
  3. washThis mixture was washed with water
  4. dry with materialdried (Na2SO4)
  5. distillationthe solvent was distilled off
  6. additionTo the residue were added acetic acid (180 ml) and hydrochloric acid (180 ml)
  7. temperaturethe mixture was heated for 5 hours at 110° C
  8. concentrationThe reaction mixture was concentrated, to which
  9. additionwas added water
  10. extractionfollowed by extraction with ethyl acetate
  11. washThe extract was washed with water
  12. dry with materialdried (Na2SO4)
  13. distillationthe solvent was distilled off
  14. customto leave colorless crystals
  15. customRecrystallization from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-97e98ab9760b46fa9d848efb477fbf6a
Source dataset
uspto-grants-1996_06
Patent number
US05527811

Reaction notes

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