Dolbier HW Solutions 467 - 561 CARBOXYLIC ACID DERIVATIVES...

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( g ) Hydrolysis of benzyl cyanide yields phenylacetic acid. Alternatively, the Grignard reagent derived from benzyl bromide may be carboxylated. ( h ) The fi rst goal is to synthesize p -nitrobenzoic acid because this may be readily converted to the desired acyl chloride. First convert toluene to p -nitrotoluene; then oxidize. Nitration must pre- cede oxidation of the side chain in order to achieve the desired para orientation. Treatment of p -nitrobenzoic acid with thionyl chloride yields p -nitrobenzoyl chloride. ( i ) In order to achieve the correct orientation in m -nitrobenzoyl chloride, oxidation of the methyl group must precede nitration. Once m -nitrobenzoic acid has been prepared, it may be converted to the corresponding acyl chloride. SOCl 2 m -Nitrobenzoic acid
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