Organic Lab Reactions 245

Organic Lab Reactions 245 - Hydroxy derivatives of biphenyl...

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240 THE PREPARATION "OF UNSYMMETRICAL BIARYLS give arylquinones. 26 By means of this reaction a number of arylquinones (and the corresponding dihydroxybiphenyls by reduction) have been prepared in 55-85% yields. 27 The solid diazonium salt is added to a solution of the quinone in alcohol, followed or preceded by the addition of an excess of sodium acetate. From diazotized aniline and benzo- quinone, phenylquinone is obtained. O 0 C«H 6 N 2 +C1- NaOAc- + N 2 + NaCl + AcOH The phenylquinone can be made to react further to give 2,5-diphenyl- quinone. 1,4-Naphthoquinone reacts readily only with reactive diazo- nium compounds such as diazotized p-aminobenzoic acid; with the latter compound it yields 2-(p-carboxyphenyl)-l,4»naphthoquinone (XXII). - O OOH XXII
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Unformatted text preview: Hydroxy derivatives of biphenyl can be prepared from diazo-nium salts, such as the chloride or sulfate, and phenols if no alkali is added. 28 ' 29 ' 30 ' 81-32 From a solution of diazotized aniline in a large excess of-phenol, a good yield of a mixture of 2- and 4-hydroxybiphenyl is obtained in addition to diphenyl ether. N 2 +C1-HC1 1 6 1 . G. Farbenind. A. G., Brit, pat., 390,029 (1933). " Kvalnes, / . Am. Chem. Soc, 56, 2478 (1934). 118 Hirsch, Ber., 23, 3705 (1890). 29 Graebe and Schestakow, Ann., 284, 306 (1895). 30 Norris, Maclntire.'and Corse, Am. Chem. J., 29, 121 (1903). 81 Chatterjee, J. Ind. Chem. Soc., 12, 410, 690 (1935). 32 Huntress and Seikel, J. Am. Chem. Soc, 61, 1066 (1939)....
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