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Organic Lab Reactions 252

Organic Lab Reactions 252 - o-CHLOROBIPHENYL 247 lized from...

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o-CHLOROBIPHENYL 247 lized from ethanol and then distilled under reduced pressure to remove .traces of the less volatile 4-methoxy isomer. It boils at 200-201 °/18 mm. 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 the mixture lowers the yield. * Procedure Utilizing Sodium Diazotate (A-2) 4-Methylbiphenyl. 4 One hundred and seven grams (1 mole) of p- 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 the addition of a solution of 76 g. of sodium nitrite in 150 cc. of water. The solution is added during the course of two to three minutes to a vigor- ously stirred mixture of 275 cc. of 10 N sodium hydroxide, 600 cc. of ben- zene, and ice sufficient to keep the temperature.at 5°. A small part of the benzene is kept frozen by the ice. When all the diazonium solution has been added, a vigorous reaction ensues, nitrogen is evolved, and the solu- tion becomes yellow.
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