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

HRID 255879Notes

Reaction equation

HRID 255879 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. dry with materialdried 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-199a2fb1ff564d64b775b69167c04b6b
Source dataset
uspto-grants-1987_10
Patent number
US04699906

Reaction notes

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