[PDF] acetylation of phenol using acetic anhydride

Phenols are not acetylated by acetic anhydride alone in carbon tetrachloride, but addition of pyridine leads to acetylation. Alcohols, in contrast, are acetylated in the absence of pyridine, but the extent of catalysis by pyridine is less than for phenols.
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  • How does phenol react with acetic anhydride?

    When acetic anhydride reacts with phenol in the presence of a base, then phenyl acetate is obtained.
  • How is acetylation with acetic anhydride done?

    In a 5 ml round-bottom flask, 1 g of 4a–h was added to an equimolar amount of acetic anhydride containing 1% of VOSO4·5H2O. The reaction was kept under stirring for 2 or 24 h at room temperature. The reaction was then quenched with 50 ml of H2O and kept under stirring for about 15 min.
  • What is the mechanism for the acetylation of an alcohol with acetic anhydride?

    Initially, acetic acid protonates the carbonyl group of acetic anhydride to give a cationic intermediate which is further attacked by the nucleophile to give an alcohol-type intermediate.
  • (iii) Acetyl chloride is more reactive and hence more liable to undergo side reaction. Therefore acetic anhydride is preferred for acylation.
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