Potassium Hydroxide → 4-Aminostyrene

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-aminophenyl)ethanol (10 g, 73 mmol), KOH (25 g, 450 mmol) and t butylcatechol (0.1 g) was heated at 240° C./40 mmHg in a flask fitted with a water-cooled condenser for 90 minutes. The contents of the flask were then distilled into a receiver vessel as a clear, 2-phase system which sodified as white crystals on standing. The solid was extracted with 50 ml diethyl ether, washed twice with 25 ml distilled water and the organic phase separated. After drying for 2 hours over NaOH pellets, the ether solution was filtered and the volatiles removed in vacuo to yield a colourless crystalline solid. Fractional distillation at 38° C. (1×10-2 mbar) yielded 4-aminostyrene. The colourless liquid was stored at -30° C. (at which temperature it is a crystalline solid) to prevent polymerisation.

Provenance & Evidence