Chloroacetone → 3-Methyl-6-(4-methylphenyl)-4,5,6,7-tetrahydrobenzofuran-4-one

HRID 1700458Notes

Reaction equation

HRID 1700458 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][C:14](=[O:16])[CH2:13][C:12](=[O:17])[CH2:11]2)=[CH:6][CH:5]=1.Cl[CH2:19][C:20](=O)[CH3:21]>CN(C)C=O>[CH3:21][C:20]1[C:13]2[C:14](=[O:16])[CH2:15][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][CH:8]=3)[CH2:11][C:12]=2[O:17][CH:19]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 5764925-(4-Methylphenyl)cyclohexane-1,3-dione

Product 1

HCID 183173083-Methyl-6-(4-methylphenyl)-4,5,6,7-tetrahydrobenzofuran-4-oneYield 21.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (10 ml) was suspended 60% sodium hydride (0.44 g, washed with hexane thrice), and to the suspension were added 5-(4-methylphenyl)cyclohexane-1,3-dione (2.0 g) and chloroacetone (0.92 g). The mixture was stirred at room temperature for 1 hour and then at 150° C. for 13 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate, water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (EtOAc/hexane), and the resulting crystals were recrystallized from hexane to give colorless crystals of 3-methyl-6-(4-methylphenyl)-4,5,6,7-tetrahydrobenzofuran-4-one (0.51 g).

Workup

  1. waitat 150° C. for 13 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. dry with materialwater and saturated brine, dried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (EtOAc/hexane)
  7. customthe resulting crystals were recrystallized from hexane

Sources & evidence

ORD record
ord-f9964bb69ac94f37b4a84beea4f3596c
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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