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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Reactions directed towards the synthesis of 5-(β-hydroxyethyl)-2-isopropylcyclohexanone

R Murphy and R Prager

Australian Journal of Chemistry 31(7) 1629 - 1634
Published: 1978

Abstract

Reduction of perillaldehyde by lithium in ammonia gives products the structures of which depend on reaction conditions. Shisool (p-menth-8- en-7-ol) undergoes double-bond migration in the presence of acids. The corresponding aldehyde, with dimethylsulfonium methylide, forms an oxiran which is comparatively unreactive, double-bond rearrangement or reduction accompanying the opening of the oxiran. The conversion of shisool into 5-(β-hydroxyethyl)-2-isopropylcyclohexanone was frustrated by only partial migration of the double bond.

https://doi.org/10.1071/CH9781629

© CSIRO 1978

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