A synthesis of tetronic acid [furan-2(3H),4(5H)-dione] and three analogues
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1225-1231
- https://doi.org/10.1039/p19720001225
Abstract
A synthesis of four tetronic acids [furan-2(3H),4(5H)-diones] is described. On treatment with triethylamine the readily prepared diethyl α-(chloroacetyl)malonate yielded ethyl 2-ethoxy-4,5-dihydro-4-oxofuran-3-carboxylate (ca. 50%), which was converted into tetronic acid by alkali, and into 3-ethoxycarbonyltetronic acid by water, in high yields. 5-Methyl-, 5-phenyl-, and 5-ethyl-tetronic acids were prepared analogously. The last compound was also obtained by hydrogenation of 5-ethylidenetetronic acid.Keywords
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