Salicylaldehyde → 5-Iodosalicylaldehyde

HRID 269592Notes

Reaction equation

HRID 269592 reaction equation
[I:1]Cl.[CH:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6].S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[OH:6][C:5]1[CH:7]=[CH:8][C:9]([I:1])=[CH:10][C:4]=1[CH:3]=[O:11]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 24437Sodium SulfiteHCID 24640Iodine chloride

Product 1

HCID 2526125-Iodosalicylaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 250 g (1.54 mol) of iodine chloride in 600 ml of anhydrous dichloromethane is added dropwise over the course of 2 h to a solution of 188 g (1.54 mol) of salicylaldehyde in 1 l of anhydrous dichloromethane in a heat-dried flask under argon. After stirring at RT for 3 days, a saturated aqueous sodium sulfite solution is added with vigorous stirring. The organic phase is separated, washed once with water and a saturated aqueous sodium chloride solution and dried over sodium sulfate. The solvent is evaporated and the residue is recrystallized from ethyl acetate. 216 g (57% of theory) of product are obtained.

Workup

  1. customThe organic phase is separated
  2. washwashed once with water
  3. dry with materiala saturated aqueous sodium chloride solution and dried over sodium sulfate
  4. customThe solvent is evaporated
  5. customthe residue is recrystallized from ethyl acetate
  6. custom216 g (57% of theory) of product are obtained

Sources & evidence

ORD record
ord-6eacb96816b3495b81af5603a00e87ab
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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