Isopropanol → Diallyl tetrabromoterephthalate

Participants

Reaction Steps

To a liquid mixture consisting of 19.3 parts of tetrabromoterephthalic acid and 40 parts of isopropyl alcohol, were added with stirring 13 parts of a 50% aqueous solution of caustic potash. After continuously mixing the thus-obtained mixture for 30 minutes, 12.6 parts of allyl bromide and 1.0 part of triethylamine were added. The resulting mixture was heated until isopropanol started to reflux. The mixture was maintained at the temperature for 8 hours. After allowing the resulting reaction mixture to cool, the liquid reaction mixture was concentrated under reduced pressures, followed by an addition of 50 parts of chloroform to dissolve the residue. The resultant solution was poured in a separation funnel and then washed with an aqueous solution of sodium bicarbonate and thereafter with water. The organic layer was concentrated and the resultant white solid was recrystallized from ethyl acetate, thereby obtaining 12 parts of diallyl tetrabromoterephthalate (hereinafter called "Compound B") as white irregular crystals (m.p. 125°-127° C.).

Provenance & Evidence