Chloroacetone → HCID 18317745, compound

HRID 1700456Notes

Reaction equation

HRID 1700456 reaction equation
[H-].[Na+].[C:3]1([CH:9]2[CH2:14][C:13](=[O:15])[CH2:12][C:11](=[O:16])[CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:18][C:19](=O)[CH3:20]>C(O)C>[CH3:20][C:19]1[C:12]2[C:13](=[O:15])[CH2:14][CH:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:10][C:11]=2[O:16][CH:18]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 5689621,3-Cyclohexanedione, 5-phenyl-

Product 1

HCID 18317745HCID 18317745, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 60% sodium hydride (0.22 g, washed with hexane thrice) was added ethanol (30 ml). To the mixture was added 5-phenylcyclohexane-1,3-dione (1.0 g) and then was added chloroacetone (0.49 g) at 0° C., and the mixture was stirred at room temperature for 20 minutes and refluxed for 13 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane) to give colorless crystals of 3-methyl-6-phenyl-4,5,6,7-tetrahydrobenzofuran-4-one (0.18 g).

Workup

  1. temperaturerefluxed for 13 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-bee3c8a7fae0436ca54d9f34e0c6be1e
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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