PRODUCTION AND PROPERTIES OF 2,3-BUTANEDIOL: XXIII. CONDENSATION OF THE ISOMERIC 2,3-BUTANEDIOLS WITH ETHYL ACETOACETATE
- 1 September 1947
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Research
- Vol. 25 (5) , 423-429
- https://doi.org/10.1139/cjr47b-049
Abstract
Levo-2,3-Butanediol will condense with ethyl acetoacetate in the presence of hydrochloric acid to give the ethyl ester of levo-2,4,5-trimethyl-2-carboxymethyl-1,3-dioxacyclopentane (I) (yield 48%) from which the free acid may be obtained. If p-toluenesulphonic acid is used as the catalyst and the condensation is carried out in boiling butanol with continuous removal of water, the butyl ester of (I) is obtained (yield 87%). Compounds described for the first time are levo-, dl-, and meso-2,4,5-trimethyl-2-carboxymethyl-1,3-dioxacyclopentanes, their n-butyl and p-bromophenacyl esters (melting points 74.5°, 76°, and 76 °C., respectively) and the ethyl ester of the levo-isomer.Keywords
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