Thermal rearrangement of 1-(3-methylbut-2-enyloxy)-4-prop-1-enylbenzene (feniculin): a new synthesis of anisoxide and re-investigation of the constituents of star anise oil
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 897-899
- https://doi.org/10.1039/p19810000897
Abstract
At 153 °C feniculin (1) undergoes Claisen rearrangement to the 1,1-dimethylallylphenol (3), which is slowly converted into the 1,2-dimethylallylphenol (4); the products of abnormal Claisen rearrangement, phenol (4) and anisoxide (2), are formed at 185 °C. Anisoxide was shown by g.l.c. analysis to be absent in star anise oil and in the seeds of Illicium verum and Foeniculum vulgare, and is believed to have been obtained previously as a result of prolonged distillation of anise oil.This publication has 0 references indexed in Scilit: