Sodium Iodide → 2-Hydroxy-5-methoxy-4-methylbenzaldehyde

HRID 493194

Reaction equation

HRID 493194 reaction equation
C[O:2][C:3]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][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]([CH3:11])[C:8]([O:12][CH3:13])=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6020192,5-Dimethoxy-4-methylbenzaldehydeHCID 6451240Aluminum(III) Chloride

Product 1

HCID 71720502-Hydroxy-5-methoxy-4-methylbenzaldehydeYield 99.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The above prepared 2,5-Dimethoxy-4-methyl-benzaldehyde (4.153 g, 23 mmol) was dissolved in 115 mL of acetonitrile and treated successively with sodium iodide (5.18 g, 1.5 eq.) and AlCl3 (3.07 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, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=9/1), gave 3.80 g of the title compound as off-white solid.

Workup

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

Sources & evidence

ORD record
ord-2522439a096745f99ad53a531b4680c5
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Linked notes

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