EFFICIENT PREPARATION OF 2-METHYL-1,3-DIOXOLANE-2-ETHANOL AND 2-(2-BROMOETHYL)-2- METHYL-1,3-DIOXOLANE FROM 4-HYDROXY-2-BUTANONE

ABSTRACT

2-Methyl-1,3-dioxolane-2-ethanol was prepared in 90% isolated yield from 4-hydroxy-2-butanone and ethylene glycol using a weak acid catalyst and ethyl acetate as the reaction solvent. 2-(2-Bromoethyl)-2-methyl-1,3-dioxolane was prepared in 75% isolated yield by bromination of 2-Methyl-1,3-dioxolane-2-ethanol with dibromotriphenylphosphorane. The reagent was prepared in situ by titrating triphenylphosphine with bromine at an ice–ethanol bath temperature. The target compounds are useful methyl vinyl ketone equivalents.

* Names are necessary to report factually on available data; however, the USDA neither guarantees nor warrants the standard of the product, and the use of the name by USDA implies no approval of the product to the exclusion of others that may also be suitable.

ACKNOWLEDGMENTS

We thank Bruce W. Zilkowski and Dr. Robert J. Bartelt for acquiring mass spectral data, David Weisleder for acquiring NMR spectra, and Dr. Robert J. Bartelt for helpful discussions.

Notes

* Names are necessary to report factually on available data; however, the USDA neither guarantees nor warrants the standard of the product, and the use of the name by USDA implies no approval of the product to the exclusion of others that may also be suitable.