Hydroxyacetone → 3-Methyl-6,7-dihydro-1-benzofuran-4(5H)-one

HRID 2121705Notes

Reaction equation

HRID 2121705 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[CH3:9][C:10]([CH2:12]O)=O>C(O)C.C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH3:12][C:10]1[C:2]2[C:1](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=2[O:7][CH:9]=1

Participants

6

Reactant 2

HCID 8299HydroxyacetoneHCID 104341,3-Cyclohexanedione

Product 1

HCID 139000243-Methyl-6,7-dihydro-1-benzofuran-4(5H)-oneYield 38%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,3-cyclohexanedione (3.36 g, 30 mmol), acetol (hydroxyacetone; 2.22 g, 30 mmol), and zinc chloride (4.09 g, 30 mmol) in ethanol (10 mL) was heated at reflux temperature for 3 hours. After cooling, the mixture was dissolved in ethyl acetate (100 mL). The whole was washed with water (100 mL), brine (100 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chlomatography eluting with ethyl acetate-hexane (1:10) to give the subtitle compound (1.69 g, 38% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 3 hours
  3. temperatureAfter cooling
  4. washThe whole was washed with water (100 mL), brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chlomatography
  8. washeluting with ethyl acetate-hexane (1:10)

Sources & evidence

ORD record
ord-94633177895e4ed99c28003f2a1f1164
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

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