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The chemistry of cycloheptatriene: Part IV: Synthesis of tropone, 2-chlorotropone and tropolone

✍ Scribed by A. P. ter Borg; R. van Helden; A. F. Bickel

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
381 KB
Volume
81
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Acid‐catalysed decomposition of tropyl ether gives tropone and cycloheptatriene in 83.5 and 90 % yields, respectively.

Chlorination of tropone in carbon tetrachloride solution yields tropone dichloride, which can be made to isomerize to the hydrochloride of 2‐chlorotropone; 2‐chlorotropone is obtained in a 83.5 % yield.

Hydrolysis of the latter compound in refluxing 80 % aqueous formic acid gives tropolone in 85 % yield.

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