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

HRID 1167637Notes

Reaction equation

HRID 1167637 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 rt 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-0c2e8ff0652f410ab40fb1209323b073
Source dataset
uspto-grants-2003_09
Patent number
US06620826B2

Reaction notes

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