Schotten-Baumann reaction, benzoylation sulphonylation

Another important aspect of Schotten-Baumann reaction is sulphonylation whereby benzene sulphonyl chloride, CgH SOgCl (i.e., the corresponding acid chloride of benzene sulphonic acid, CgH SOgOH) is employed instead of benzoyl chloride, and almost similar structural analogues may be obtained. 

The Schotten-Baumann reaction may also be carried out, using, for example, benzene sulphonyl chloride, CeH,SO,Cl (. e., the acid chloride of benzene sulphonic acid, C H5SOjOH) in place of benzoyl chloride, and similar deri a-tives are obtained. Thus when phenol is dissolved in an excess of 10% sodium hydroxide solution, and then shaken with a small excess of benzene sulphonyl... 

Give benzoyl and toluene-/>-sulphonyl derivatives (Schotten-Baumann reaction) (p. 243) also benzene-sulphonyl derivatives. 

The Schotten-Baumann reaction can also be applied to primary and secondary aromatic amines (see p. 303) it is much used in the identification of compounds to which it can be applied, by the preparation of their benzoyl, phenylacetyl, or benzene sulphonyl derivatives. 

The full paper concerning the reaction of acyl chlorides (benzoyl and toluene-p-sulphonyl chlorides) with the steroidal nitrone derivative (23) of conanine has been published. Additional information concerning the mechanism of these reactions is given. Thus, it was shown that the formation of the a -benzyloxyimine (24) needs acidic conditions which favour the heterolysis of the N—O bond (Scheme 2). At room temperature, under Schotten-Baumann conditions, the epimeric compounds (25) were obtained from (23) with benzoyl chloride. Compound (25) gave (24) on refluxing in neutral solvent or by treatment with acid, whereas (24) was obtained directly from (23) when treated with a benzene solution of benzoyl chloride in the presence of aqueous sulphuric acid. 

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See also in sourсe #XX -- [ ]

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