Methyl iodide → 4-methoxy-2,3-dihydro-1H-inden-1-one

HRID 1905728Notes

Reaction equation

HRID 1905728 reaction equation
CI.[OH:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:13].[C:14](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:14][O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 45474914-methoxy-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Methyl iodide (69 ml) is added dropwise over a period of 15 minutes to a stirred mixture of 4-hydroxy-1-indanone (150 g) and anhydrous potassium carbonate (154 g) dissolved in DMF (1.5 liter) cooled to 0° C. under nitrogen. The reaction mixture is stirred at RT for 24 hours and partitioned between methylene chloride and water. The methylene chloride fraction is washed with water and 2% aqueous NaOH and dried over NA2SO4. The dried extract is filtered, concentrated in vacuo and the residue dissolved in hot methanol which upon cooling forms a precipitate. The precipitate is filtered and recrystallized from methanol yielding the methoxy product as a solid, M.P. 104°-106° C.

Workup

  1. custompartitioned between methylene chloride and water
  2. washThe methylene chloride fraction is washed with water and 2% aqueous NaOH
  3. customdried over NA2SO4
  4. extractionThe dried extract
  5. filtrationis filtered
  6. concentrationconcentrated in vacuo
  7. dissolutionthe residue dissolved in hot methanol which
  8. temperatureupon cooling forms a precipitate
  9. filtrationThe precipitate is filtered
  10. customrecrystallized from methanol yielding the methoxy product as a solid, M.P. 104°-106° C.

Sources & evidence

ORD record
ord-ff79388f057048baa3fa122345a97108
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

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