Sodium Iodide → 84422-52-6

HRID 493208Notes

Reaction equation

HRID 493208 reaction equation
C[O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([CH3:13])=[CH:7][C:4]=1[CH:5]=[O:6].[I-].[Na+].[Al+3].[Cl-].[Cl-].[Cl-]>C(#N)C>[OH:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([CH3:13])=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 2516922,4-Dimethoxy-5-methylbenzaldehydeHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1316681984422-52-6

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The above prepared 2,4-Dimethoxy-5-methyl-benzaldehyde (5.40 g, 30 mmol) was dissolved in 150 mL of acetonitrile and treated successively with sodium iodide (6.74 g, 1.5 eq.) and AlCl3 (4.00 g, 1.0 eq.), and the mixture kept at 80° C. for 1 h. Cooling, pouring onto crashed ice, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=9/1), delivered 4.23 g of the title compound as light brown crystals.

Workup

  1. temperatureCooling
  2. additionpouring
  3. extractionice, twofold extraction with AcOEt
  4. washwashing with water and brine
  5. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-11a5a2acbeae4b778a041cb41b2954dc
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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