Question

Explain what might cause difficulties using esterification to prepare isopropyl formate and n-butyl formate

(hint: check the physical properties of the reagents and products)

Answer 1

Esterification reaction is reversible in the presence of water. Esterification reaction to prepare isopropyl formate and n-butyl formate  is performed in the liquid phase at elevated pressure. Typical reaction conditions are 80 °C and 40 atm.

Efficient hydrolysis of isopropyl formate and n-butyl formate requires a large excess of water. Some routes proceed indirectly by first treating the isopropyl formate or n-butyl formate with ammonia to give formamide, which is then hydrolyzed with sulfuric acid. A disadvantage of this approach is the need to dispose of the ammonium sulfate byproduct.