Carbon Dioxide → 4-Vinylphenol

Participants

Reaction Steps

Para-vinylphenol was prepared as follows. 15.6 g of p-hydroxycinnamic acid were mixed to a slurry with 15 ml quinoline, 0.6 g copper turnings and 1.1 g hydroquinone. The mixture was heated by an oil bath at 200° C. for 15 minutes after which time the evolution of CO2 had almost ceased. The reaction mixture was then cooled and distilled under rotary pump vacuum, the fraction collected between 60° and 80° C. being p-vinylphenol and quinoline. (Bpt. Quinoline=114° C./15 mm Hg; p-vinylphenol=115° C./16 mm Hg). The distilled fraction was taken up into warm diethyl ether, the solution neutralised by successive washing of N HCl and distilled water and then dried by MgSO4. After removal of the solvent, the residue was redissolved by warm petroleum ether (40°-60° C.). On cooling 1.36 g of colourless, platey crystals were obtained. Yield=11.76%. These were recrystallised from the same solvent prior to copolymerisation.

Provenance & Evidence