Potassium Hydroxide → HCID 14495373, compound

Participants

Reaction Conditions

Reaction Steps

A 15.0g (72.61 mmol) portion of 3-(cyclopent-2-enyl)-2,6-toluenediamine was added to a 250cc round bottomed flask containing 1.50g (22.7 mmol) of 85% potassium hydroxide, 16.79 (278.0 mmol) isopropanol, 100cc of mixed xylenes. The mixture was stirred at room temperature under a static nitrogen atmosphere until all the potassium hydroxide had dissolved. The flask was fitted with a Claisen distillation head, a condenser, a receiving flask and then warmed to 115°. Isopropanol and water were removed over a 2 hour period. The temperature of the reaction flask was then raised to 160° C. and maintained for a period of 5 hours. During this period, the mixed xylenes were slowly removed by atmospheric distillation. The product was then isolated from the flask by bulb-to-bulb distillation at 160°-180° C. 10.5mm Hg. An 11.5g sample (76.7% isolated yield) of the α-β-unsaturated product was obtained.

Provenance & Evidence