The Synthesis and Reactions of 2-Chloro-5-hydroxytropone
- 1 June 1966
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 39 (6) , 1310-1316
- https://doi.org/10.1246/bcsj.39.1310
Abstract
The acid hydrolysis of some polyhalotropones and some reactions of the products were investigated. The treatment of 2,5-dichlorotropone with hydrochloric or sulfuric acid afforded 2-chloro-5-hydroxytropone (I) and a small amount of 5-chlorotropolone. The compound I gives only one kind of the methyl ether and one kind of the acetyl or benzoyl derivative. From the methyl ether, 5-amino- and 5-methylamino-2-chlorotropone were derived. The methoxyl and the amino groups of these compounds are reactive to alkaline hydrolysis, giving I without any of the skeletal rearrangement usually observed in the alkaline treatment of similar 2-halotropones. The hydrolysis of 2,4,7-tribromotropone with hydrochloric acid gave 3,6-dichlorotropolone and 7-chloro-4-hydroxytropolone.Keywords
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