Acetone → HCID 10266436, compound

HRID 259748Notes

Reaction equation

HRID 259748 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)C=O>[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), dimethylformamide (10 ml), potassium carbonate (6.83 g) and diethyl bromomalonate (12.84 g) was stirred at room temperature for 60 hours. The solvent was then distilled off and ethyl acetate was added to the residue. The mixture was washed with water and dried (Na2SO4) and the solvent was distilled off. To the residue were added acetic acid (180 ml) and hydrochloric acid (180 ml) and the mixture was heated at 110° C. for 5 hours. The reaction mixture was then concentrated and the concentrate was diluted with water and extracted with ethyl acetate. The extract was washed with water and dried (Na2SO4) and the solvent was distilled off. The resulting crystals were recrystallized from ethyl acetate-isopropyl ether to provide the title compound. Melting point: 265°-268° C.

Workup

  1. distillationThe solvent was then distilled off
  2. additionethyl acetate was added to the residue
  3. washThe 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 at 110° C. for 5 hours
  8. concentrationThe reaction mixture was then concentrated
  9. additionthe concentrate was diluted with water
  10. extractionextracted with ethyl acetate
  11. washThe extract was washed with water
  12. dry with materialdried (Na2SO4)
  13. distillationthe solvent was distilled off
  14. customThe resulting crystals were recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-a2bcc79351f14c3d95d29cacb992c3f7
Source dataset
uspto-grants-1996_06
Patent number
US05523305

Reaction notes

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