Reaction #2275671

Reaction equation

p-toluenesulfonic acid

4-hydroxy-2-methoxybenzaldehyde

benzenesulfonamide

toluene

→

N-[(4-hydroxy-2-methoxyphenyl)methylidene]benzenesulfonamide

Solvents

water

water

Conditions

Workup

1. 1
   TemperatureThe mixture was then heated
2. 2
   Otherhad separated
3. 3
   Filtrationthe precipitated solid was filtered off
4. 4
   Otherdried under vacuum

Procedure

An equimolar mixture of 27.4 g (0.18 mol) 4-hydroxy-2-methoxybenzaldehyde and 28.3 g (0.18 mol) benzenesulfonamide was placed into toluene. 100 mg p-toluenesulfonic acid was added as a catalyst. The mixture was then heated under reflux on a water separator until the theoretically calculated quantity of water had separated. After cooling to room temperature, the precipitated solid was filtered off and dried under vacuum. Yield: 43.0 g (78.9%).

Source