PRODUCTION AND PROPERTIES OF 2,3-BUTANEDIOL: XXIII. CONDENSATION OF THE ISOMERIC 2,3-BUTANEDIOLS WITH ETHYL ACETOACETATE
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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.
2018 ◽
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1977 ◽
Vol 32
(3)
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pp. 311-314
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2011 ◽
Vol 2011
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pp. 1-6
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2010 ◽
Vol 10
(10)
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pp. 23017-23043
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2018 ◽
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Keyword(s):
1995 ◽
Vol 1259
(3)
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pp. 297-304
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