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By George H. Schenk

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5 M acetyl chloride in toluene; pyridine was added separately to catalyze the reaction, as it formed a precipitate with acetyl chloride. Quantitative acetylation required 20 min at 60°C. It was shown that acetyl chloride was more reactive than acetic anhydride by comparing their reaction rates with 2,4-dimethylpentan-3-ol. 9% complete with the anhydride. Smith and Bryant did not report quantitative results for amines but appear to indicate that they react to varying degrees with acetyl chloride.

In contrast, Valentin used acetic anhydride in dioxane and fluoboric acid catalyst and obtained quantitative results after 5 min heating on the steam bath. ( 3 8) In 1942 Toennies, Kolb, and Sakami reported perchloric acid-catalyzed acetylation in glacial acetic acid of hydroxyl groups on amino acids, but again their conditions were such that the method required 2 hr at room temperature. Thus, the full potential of this catalyst remained unrealized; it was to remain thus for 17 more years. 48 ORGANIC FUNCTIONAL GROUP ANALYSIS MECHANISM OF ACID-CATALYZED ACETYLATION An understanding of the mechanism of any analytical reaction enables the analyst to: (a) Select optimum conditions for the method.

Aromatic amines react less rapidly, requiring a short period of heating or longer reaction times at room temperature with all reagents but 3,5-dinitrobenzoyl chloride. If amines are nucleophilic enough to be determined by acylation, they are also generally basic enough to be titrated with perchloric acid in a nonaqueous solvent. Researchers have thus concentrated on using acylating agents for the determination of less nucleophilic alcohols and phenols. ( 1 6) Mehlenbacher has reviewed acylation methods as recent as ( 1 5 a) 1952, and M a t h u r has reviewed methods which have ap( 2 8) ( 3) peared since 1955.

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