Methyl iodide → 2,6-Dichloro-4-methoxybenzaldehyde

HRID 1171143Notes

Reaction equation

HRID 1171143 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].[C:12](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:12])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5283822,6-Dichloro-4-hydroxybenzaldehyde

Product 1

HCID 147717592,6-Dichloro-4-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 2,6-dichloro-4-hydroxy-benzaldehyde (120 g, 628.24 mmol) and potassium carbonate (173.65 g, 1256.5 mmol) in 900 mL dimethylformamide and treat with iodomethane (107 g, 753.9 mmol). Stir the reaction at room temperature for 3 hours. Filter off solids and pour into 6 L of water. Filter solids, wash several times with water, air dry and dissolve in ethyl acetate. Wash with water, followed by brine and then dry over sodium sulfate. Filter and concentrate under vacuum to ˜100 mL volume, at which point, solids start to crash out. Filter then concentrate down the filtrate to yield a second crop. Wash with hexane, combine all solids and vacuum dry to yield 112.3 g of off-white, solid: 1H NMR (400 MHz, CDCl3) δ 10.41 (s, 1H), 6.90 (s, 2H), 3.87 (s, 3H).

Workup

  1. customthe reaction at room temperature for 3 hours
  2. filtrationFilter off solids
  3. additionpour into 6 L of water
  4. filtrationFilter solids
  5. washwash several times with water, air
  6. customdry
  7. dissolutiondissolve in ethyl acetate
  8. washWash with water
  9. dry with materialdry over sodium sulfate
  10. filtrationFilter
  11. concentrationconcentrate under vacuum to ˜100 mL volume, at which point, solids
  12. filtrationFilter
  13. concentrationthen concentrate down the filtrate
  14. customto yield a second crop
  15. washWash with hexane
  16. customdry
  17. customto yield 112.3 g of off-white, solid

Sources & evidence

ORD record
ord-768498fa1e2544bbb95352304b4441a1
Source dataset
uspto-grants-2010_11
Patent number
US07829582B2

Reaction notes

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