Salicylaldehyde → 5-Iodosalicylaldehyde

HRID 2756

Reaction equation

HRID 2756 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].ClCl.[I:12]Cl.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[OH:4][C:3]1[CH:5]=[CH:6][C:7]([I:12])=[CH:8][C:2]=1[CH:1]=[O:9]

Participants

6

Reactant 4

HCID 6998SalicylaldehydeHCID 24437Sodium SulfiteHCID 24526ChlorineHCID 24640Iodine chloride

Product 1

HCID 2526125-Iodosalicylaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of salicylaldehyde (10 g, 82 mmol) in 50 mL of CH2 Cl2 is added 22 mL of a 1M ICl solution in CH2Cl2. The solution is stirred for 14 h. 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-8ec2d97e687846619b32961cdb968717
Source dataset
uspto-grants-1998_03
Patent number
US05731315

Linked notes

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