Salicylaldehyde → 5-Iodosalicylaldehyde
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe layers are separated
- washThe organic layer is washed with water
- dry with materialThe organic layer is dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe resulting crude material is recrystallized from cyclohexane
Sources & evidence
- ORD record
- ord-8ec2d97e687846619b32961cdb968717
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05731315
Reaction notes
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