Organic Lab Reactions 239

Organic Lab Reactions 239 - hydrolysis. By coupling...

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234 THE PREPARATION OF UNSYMMETRICAL BIARYLS It is* not possible to prepare biaryls containing a free carboxyl group directly by the diazo reaction. No biaryl is formed when (a) diazotized aniline and sodium benzoate, (6) diazotized anthranilic acid and aqueous sodium benzoate, or (c) diazotized anthranilic acid and benzene are used as components in the reaction. 13 On the other hand, the reaction pro- ceeds normally if methyl benzoate is used in reaction (a) or when methyl anthranilate replaces the anthranilic acid in (b) and in (c). The success of the diazohydroxide reaction appears to lie in the ability of the non- aqueous liquid to extract the reactive diazo compound from the aqueous layer. 4 However, esters and nitriles can be prepared from esters of aromatic amino acids and cyanoanilines and also by coupling with esters of aromatic acids, and from the products the acids can be obtained by
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Unformatted text preview: hydrolysis. By coupling N-nitrosoacetanilide with ethyl phthalate, ethyl 4-phenylphthalate (VIII) is formed in 37% yield. VIII The products obtained from esters of anthranilic acid and substituted anthranilic acids are of interest because fluorenones can be prepared from them. From diazotized methyl anthranilate and benzene, 2-carbometh-oxybiphenyl is obtained in 24% yield. Hydrolysis affords 2-biphenylcar-boxylic acid, which can be cyclized to fluorenone. By this procedure, a number of 2- and 3-substituted fluorenones have been prepared. 16 Thus, 3-chlorofluorenone was prepared from methyl 4-chloroanthranilate and benzene through the following steps. ,-COOCH Cl . .COOCH. "HeUbron, Hey, and Wilkinson, J Chem Soc , 1938, 113,...
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This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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