Salicylaldehyde → 5-Iodosalicylaldehyde

HRID 1636774Notes

Reaction equation

HRID 1636774 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[I:10]Cl.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[OH:4][C:3]1[CH:5]=[CH:6][C:7]([I:10])=[CH:8][C:2]=1[CH:1]=[O:9]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 24437Sodium SulfiteHCID 24640Iodine chloride

Product 1

HCID 2526125-Iodosalicylaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of salicylaldehyde (10 g, 82 mmol) in 50 mL of CH2Cl2 is added 22 mL of a 1 M ICl solution in CH2Cl2. The solution is stirred for 14 hours. After this time, a saturated solution of sodium sulfite is added until the color is discharged. The solution is diluted with CH2Cl2. The layers are separated. The organic layer is washed with water. The organic layer is dried over MgSO4, filtered and concentrated. The resulting crude material is recrystallized from cyclohexane to give the title compound (7.2 g, 32 mmol) as white solid.

Workup

  1. customThe layers are separated
  2. washThe organic layer is washed with water
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude material is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-d0ab80137c8248338138ec883ab3b747
Source dataset
uspto-grants-2000_03
Patent number
US06034093

Reaction notes

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