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

HRID 365350Notes

Reaction equation

HRID 365350 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 95,850.102%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sesamol (10.0 g, 0.072 mmol) 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-cb3792366a024099857356522b67597c
Source dataset
uspto-grants-2000_10
Patent number
US06127371

Reaction notes

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