p-Toluenesulfonic acid → 4-[1-(2-Hydroxyphenyl)ethylideneamino]-3-methylphenol

Participants

Reaction Steps

To a 1 liter round bottom flask equipped with a water collector, water condenser, magnetic stirrer and drying tube was added 12.32 grams (0.10 mole) of 4-amino-3-methylphenol, 14.30 grams (0.105 mole) of 2-hydroxyacetophenone, 0.6 grams (0.005 moles) of p-toluenesulfonic acid and 500 milliliters of toluene. The resulting reaction mixture was stirred and refluxed for 100 hours during which time water was collected from the reaction. After the stirring and refluxing period, the reaction mixture was cooled to room temperature, filtered and left standing for 50 hours forming a solid material. The resulting solidified material was removed by filtration and recrystallized from toluene to give 10.10 grams (0.042 moles) of 4-[1-(2-hydroxyphenyl)ethylideneamino]-3-methylphenol having a melting point of 144°-156° C.

Provenance & Evidence