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PRODUCTION AND PROPERTIES OF 2,3-BUTANEDIOL: XXIII. CONDENSATION OF THE ISOMERIC 2,3-BUTANEDIOLS WITH ETHYL ACETOACETATE

 

作者: A. C. Neish,  

 

期刊: Canadian Journal of Research  (NRC Available online 1947)
卷期: Volume 25b, issue 5  

页码: 423-429

 

ISSN:1923-4287

 

年代: 1947

 

DOI:10.1139/cjr47b-049

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

levo-2,3-Butanediol will condense with ethyl acetoacetate in the presence of hydrochloric acid to give the ethyl ester oflevo-2,4,5-trimethyl-2-carboxymethyl-1,3-dioxacyclopentane (I) (yield 48%) from which the free acid may be obtained. Ifp-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 arelevo-,dl-, andmeso-2,4,5-trimethyl-2-carboxymethyl-1,3-dioxacyclopentanes, theirn-butyl andp-bromophenacyl esters (melting points 74.5°, 76°, and 76 °C., respectively) and the ethyl ester of thelevo-isomer.

 

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