Benzoyl-1,2,4-triazole underwent esterification with a primary alcohol in the presence of 4-(N,N-dimethylamino)pyridine (DMAP) catalyst at the rate comparable to benzoyl chloride. The kinetic study concluded that the reaction proceeds in a similar mechanism to carboxylic acid anhydride and is thus sensitive to the steric hindrance of alcohol. As the esterification of benzoyl-1,2,4-triazole did not afford acidic by-product and require an equimolar or more amount of base, it is effective for the protection of acid-sensitive alcohol and polyester synthesis.

Esterification with benzoyl-1,2,4-triazole, catalyzed by weak bases, effectively protects acid-sensitive alcohol and polyester synthesis without producing acidic by-products.

Paper

Esterification with Aromatic Acyl-1,2,4-triazole Catalyzed by Weak Base at the Rate Comparable to Acyl Chloride

References

Citations