Reaction #75367

Reaction equation

p-Toluidine

acetophenone

→

N-(α-methylbenzylidene)-p-toluidine

Solvents

toluene

Conditions

Workup

1. 1
   OtherThe required amount of water had been removed after 3 hours
2. 2
   OtherThe solvent was removed on the rotary, and the residue
3. 3
   workup.DISTILLATIONwas distilled under reduced pressure

Procedure

p-Toluidine (0.20 mole), acetophenone (0.20 mole), and IRC-50 (weakly acidic) ion exchange resin (0.5 g.) were azeotropically refluxed in toluene (150 cc). The required amount of water had been removed after 3 hours. The solvent was removed on the rotary, and the residue was distilled under reduced pressure to give N-(α-methylbenzylidene)-p-toluidine. b.p. 129°-37° C./0.05 mm.

Source