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Organic Lab Reactions 249

Organic Lab Reactions 249

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244 ' THE PREPABATION OF UNSYMMETRICAL BIARYLS amines: the nitroanilines, o-chloroaniline, and 0-naphthylamine, as shown in the following table. All the reactions were with benzene. COMPARISON OP YIELDS USING SODIUM HYDROXIDE AND SODIUM -ACETATE Yields Amine Aniline o-Nitroaniline wi-Nitroaniline p-Nitroaniline o-Chloroaniline m-phloroaniline p-Chloroaniline p-Toluidine p-Bromoaniline p-Anisidine p-Phenetidine jS-Naphthylamine Product Biphenyl 2-Nitrobiphenyl 3-Nitrobiphenyl 4-Nitrobiphenyl 2-Chlorobiphenyl 3-Chlorobiphenyl 4-Chlorobiphenyl 4-Methylbiphenyl 4-Bromobiphenyl 4-Methoxybiphenyl 4-Ethoxybiphenyl jS-Phenylnaphthalene NaOH 22% 21 18 26 25 25 40 22 44 25 29 16 CH 8 COONa 16% 45 45 60 38 13 35 11 12 4 11 25 The effect of various other reagents on the yield of biphenyl from diazotized aniline and benzene has been studied. The following yields of biphenyl were obtained from one mole of aniline under the conditions noted. 16 ' 46 REAGENTS METHOD YIELD OP BIPHENYL NaOH Diazohydroxide 22% NaOH Diazotate 24 Ca(OH) 4 Diazohydroxide 29 Ca(OH) 2 Diazotate 22 Mg(0H) 2 Diazohydroxide 33 MgSQ*, then NaOH Diazohydroxide 35 Grieve and Hey 13 obtained no markedly improved yields
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