Chloroacetone → HCID 18317334, compound

HRID 1700463Notes

Reaction equation

HRID 1700463 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[CH2:12][C:11](=[O:16])[CH2:10]1.[H-].[Na+].Cl[CH2:20][C:21](=O)[CH3:22]>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[C:12]2[C:21]([CH3:22])=[CH:20][O:16][C:11]=2[CH2:10]1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 183177375-(2,5-Dimethylphenyl)-1,3-cyclohexanedione

Product 1

HCID 18317334HCID 18317334, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2,5-dimethylphenyl)cyclohexane-1,3-dione (mp194-195° C.; 1.08 g) in DMF (20 ml) was added 60% sodium hydride (0.22 g), and the mixture was stirred, under argon atmosphere, at room temperature for 15 minutes. To the mixture was added chloroacetone (0.45 ml), and the mixture was stirred at 150° C. overnight (16 hours). The reaction solution was cooled, and to the mixture was added ice-water. The mixture was extracted with ethyl acetate. The upper layer was washed with saturated brine, dried (anhydrous magnesium sulfate), and concentrated under reduced pressure, and the residue was subjected to silica gel chromatography and eluted with ethyl acetate/hexane to give 6-(2,5-dimethylphenyl)-3-methyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.36 g).

Workup

  1. stirringthe mixture was stirred at 150° C. overnight (16 hours)
  2. temperatureThe reaction solution was cooled
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe upper layer was washed with saturated brine
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. washeluted with ethyl acetate/hexane

Sources & evidence

ORD record
ord-6e32494256884c179abf6356f66e9fb9
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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