244 PRACTICAL ORGANIC CHEMISTRY Thus phenol when subjected to the Schotten-Baumann reaction first dis-solves in the sodium hydroxide to give sodium phenoxide, which then undergoes C 6 H 5 COCl + NaOC 6 H 5-> C 6 H 5 COOC 6 H 5 + XaCl bcnzoylation to give phenyl benzoate. An aqueous suspension of aniline similarly gives benzoyl-aniline, or phenyl-benzamide (frequently called benz-C 6 H 5 NHH + ClCOC 6 H 5-> C 6 H 5 NHCOC 6 H 5-f HCl anilide); whilst monomethylaniline gives benzoyl-monomethylaniline or C 6 H 5 N(CH 3 )H -f ClCOC 6 H 3-> C 6 H 5 X(CH 3 )COC 6 H 5 + HCl A 7-methylphenylbenzamide. Tertiary amines clearly cannot react in this way. When these benzoyl compounds separate in the course of the Schotten-Baumann reaction, they frequently occlude traces of unchanged benzoyl chloride, which thus escapes hydrolysis by the alkali: it is advantageous there-fore to recrystallise the benzoyl compounds whenever possible from ethanol or methylated spirit, since these solvents will esterify the unchanged chloride
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This note was uploaded on 09/19/2011 for the course CHM 2211 taught by Professor Castalleano during the Fall '06 term at University of Florida.