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

HRID 1857566Notes

Reaction equation

HRID 1857566 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 (10.00 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 (13.50 mL, 0.22 mo) 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 (10.50 g, 96%); 1H NMR (250 MHz, CDCl3) δ 6.70 (d, J=20 Hz, 1H), 6.55 (d, 1H), 6.30 (dd, 1H), 5.88 (s, 2H), 3.90 (s, 3H); TLC Rf 0.72 (silica gel, 1:1 ether:hexane).

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-f02e55ccfc6144508d87bf6bb29f2d0b
Source dataset
uspto-grants-2000_11
Patent number
US06147111

Reaction notes

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