DBU-CH₃I, a Potential Substitute for CH₂N₂ in the Preparation of Methyl Esters and Methyl Aryl Ethers: Studies with Assorted Acids

Abstract

DBU-CH₃I has been poised to be a substitute for diazomethane in the preparation of methyl esters from carboxylic acids. The reactions can be carried out in commercial untreated acetone and acetonitrile, which have been exemplified with several methyl esters, otherwise it is difficult to prepare. Bis-esterification using diiodomethane can also be achieved in a similar fashion. Sufficiently acidic phenols are also conveniently O-methylated by the method.

Keywords:

• DBU
• diiodomethane
• iodomethane
• phenols
• phthalaldehydic acids
• pyridine carboxylic acids

ACKNOWLEDGMENTS

The authors are grateful to the department of Science and Technology, New Delhi, for financial support. A. J. thanks University Grants Commission for the research fellowship. S. R., A. P., and S. R. D. thank Council of Scientific and Industrial Research for their research fellowships.

Notes

^a Yields refer to the isolated yields.

^b Diiodomethane.

^c Mixture of cis and trans isomers.

^d 3,3-Dimethyl-3-chloropropyne.