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Organic Lab Reactions 253

Organic Lab Reactions 253 - 248 THE PREPARATION OF...

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248 THE PREPARATION OF UN8YMMETRICAL BIARYLS i ; Procedure Utilizing a Stabilized Diazonium Salt (A-4) a-Phenylnaphthalene. 6 a-Naphthylamine (14.3 g.) is diazotized at 0° in a mixture of 24 cc v of hydrochloric acid (sp. gr. 1.16) and 150 cc. of water, and the diazonium salt solution is treated with 16 g. of finely powdered naphthalene-l,5-disulfonic acid. Some stabilized diazonium salt separates immediately, but the mixture is stirred for one hour to complete the precipitation. The salt is then filtered and dried. To 10 g. of the dry salt, well agitated with 30 g. of benzene, at room temperature, are added 3 g. of anhydrous sodium acetate and 1 g. of acetic anhydride. After forty-eight hours, the mixture is heated to 80° until nitrogen ceases to be evolved, the mixture is treated with water, the benzene layer is separated, the solvent is removed, and the a-phenyl- naphthalene"is isolated (no details given); yield, 1.4 g. (30%). Procedure with Pyridine (A-5)
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