o-CHLOROBIPHENYL 247lized from ethanol and then distilled under reduced pressure to remove.traces of the less volatile 4-methoxy isomer. It boils at 200-201 °/18mm. and melts at 63-64°; yield, 64 g. (20%).The 4-methoxy-4'-bromobiphenyl is recrystallized from benzene-ethanol; yield, 22 g. (7%); m.p. 144-145°. Direct distillation of themixture lowers the yield. *Procedure Utilizing Sodium Diazotate (A-2)4-Methylbiphenyl.4One hundred and seven grams (1 mole) ofp-toluidine is dissolved in 185 cc. of concentrated hydrochloric acid (sp. gr.1.2), the solution is cooled by the addition of ice and diazotized by theaddition of a solution of 76 g. of sodium nitrite in 150 cc. of water. Thesolution is added during the course of two to three minutes to a vigor-ously stirred mixture of 275 cc. of 10Nsodium hydroxide, 600 cc. of ben-zene,and ice sufficient to keep the temperature.at 5°. A small part of thebenzene is kept frozen by the ice. When all the diazonium solution hasbeen added, a vigorous reaction ensues, nitrogen is evolved, and the solu-tion becomes yellow.
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