Cl₃CCONH₂/PPh₃: A Versatile Reagent for Synthesis of Esters

Abstract

Cl₃CCONH₂/PPh₃ was a versatile reagent to convert carboxylic acids into their corresponding acid chlorides. This intermediate was clearly confirmed by spectroscopic methods (IR, ¹H, ¹³C NMR). This one-pot reaction of in situ acid chloride generated with various alcohols successfully furnished the corresponding esters in moderate to excellent yields.

Keywords:

• Acid chloride
• ester
• one-pot conversion
• PPh₃
• trichloroacetamide

ACKNOWLEDGMENTS

Financial support from the Thailand Research Fund through the Royal Golden Jubilee Ph.D. Program (Grant No. PHD/0223/2548) to O. C. and W. C. is acknowledged. O. C. and W. C. are also indebted to the Graduate School, Chulalongkorn University, for a grant. One of us (D. O. J.) is also grateful for the support from Institute for NanoBio Molecular Assemblies.

Notes

^a 3 equiv of t-butylalcohol and 6 h for step 2 were used.

^a 1.2 equiv of acetic acid.

^b 2 equiv of acetic acid.

^c Room temperature (28–30°C) in step 2.

^a Step 2 for 3 h.