Tandem One-Pot Conversion of Aldehydes into Ethyl Esters

Abstract

A facile one-pot synthesis of ethyl esters from aldehydes has been developed. This tandem process involves the formation of a nitrile intermediate obtained from the reaction of an aldehyde with hydroxylamine hydrochloride in dimethylsulfoxide (DMSO) at 100 °C and the subsequent reaction of the nitrile with ethanol and sulfuric acid at 130 °C. The resulting ethyl ester products were produced in good yields (65–90%) and high purity (>95%).

Keywords:

• Aldehyde
• ethyl ester
• nitrile
• nitrile alcoholysis
• tandem reaction

ACKNOWLEDGMENTS

The authors gratefully acknowledge financial support from the Research Corporation, the University of Chattanooga Foundation, and the Grote Chemistry Fund.

Notes

^a Aldehyde (2.0 mmol), NH₂OH · HCl (3.8 mmol), DMSO (4 mL), ethanol (10 mL), and H₂SO₄ (5 mL).

^b Isolated yields.

^c Total time for complete reaction = 3 h.

^d Total time for complete reaction = 3.5 h.