What question did this study set out to answer?

To determine the mechanism and kinetic behavior of pyridine catalysis in the acetylation of phenols and alcohols by acetic anhydride.

January 1, 1968Journal of the Chemical Society B Physical Organic

The pyridine-catalysed acetylation of phenols and alcohols by acetic anhydride

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To determine the mechanism and kinetic behavior of pyridine catalysis in the acetylation of phenols and alcohols by acetic anhydride.
Monitored acetylation of phenols (specifically p-chlorophenol) and alcohols with acetic anhydride in carbon tetrachloride.
Evaluated reaction rates in the presence and absence of pyridine across varying catalyst concentrations.
Phenols exhibit zero acetylation with acetic anhydride alone in carbon tetrachloride, but acetylate upon the addition of pyridine.
Alcohols acetylate without a catalyst, though pyridine accelerates the reaction to a lesser extent than observed with phenols.
Acetylation rate of p-chlorophenol reaches a defined maximum as pyridine concentration increases, consistent with catalysis occurring exclusively via a hydrogen-bonded phenol complex.

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Implication

Mechanistic study reveals pyridine-dependent acetylation rates in phenols and alcohols, indicating a pathway mediated by hydrogen-bonded intermediates.

Cite This Study

Bonner et al. (1968) studied this question.

synapsesocial.com/papers/6a9d7991612f7f644148b079 https://doi.org/10.1039/j29680000795

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Implication

Mechanistic study reveals pyridine-dependent acetylation rates in phenols and alcohols, indicating a pathway mediated by hydrogen-bonded intermediates.

The pyridine-catalysed acetylation of phenols and alcohols by acetic anhydride

Key Points

Discussion

Implication

Cite This Study

The pyridine-catalysed acetylation of phenols and alcohols by acetic anhydride

Key Points

Discussion

Implication

Cite This Study

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