Reaction #2852

Reaction equation

sodium sulfite

salicylaldehyde

Cl2

ICl

→

title compound

2-Hydroxy-5-iodo-benzaldehyde

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   OtherThe layers are separated
2. 2
   WashThe organic layer is washed with water
3. 3
   DryingThe organic layer is dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   OtherThe resulting crude material is recrystallized from cyclohexane

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.

Source