Methyl iodide → 1,3-Benzodioxole, 5-methoxy-

HRID 1586025Notes

Reaction equation

HRID 1586025 reaction equation
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:3]=2[O:2]1.[H-].[Na+].I[CH3:14]>CN(C=O)C>[CH3:14][O:10][C:7]1[CH:8]=[CH:9][C:3]2[O:2][CH2:1][O:5][C:4]=2[CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68289Sesamol

Product 1

HCID 5924531,3-Benzodioxole, 5-methoxy-Yield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sesamol (10.0 g, 0.072 mol) in DMF (50 ml) was added sodium hydride (2.08 g, 0.087 mol) at room temperature under argon. After stirring for 1 h, the mixture was treated with iodomethane (13.5 ml, 0.216 mol) and stirred for another 18 h. Upon the removal of the solvent the residue was extracted with ethyl acetate and washed with water, dried (Na2SO4) and concentrated to afford the title compound as a dark brown oil (10.5 g, 96%).

Workup

  1. stirringstirred for another 18 h
  2. customUpon the removal of the solvent the residue
  3. extractionwas extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c646ac5e415443699e817a89927e734d
Source dataset
uspto-grants-1999_08
Patent number
US05942516

Reaction notes

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