SCHEDULED MAINTENANCE:
The synthesis of the racemate of the naturally occurring phenol, bakuchiol, p-(3,7-dimethyl-3-vinylocta-trans-1,6-diimyl)phenol, is reported. The key step was the in situ formation and Claisen rearrangement of the geranyl enol ether of acetophenone to 1-p-methoxyphenyl-3,7-dimethyl-3-vinyloct-6-en-1-one (IIIa). Bakuchiol cyclised readily in the presence of acid.
J. Carnduff and J. A. Miller, J. Chem. Soc. C, 1968, 2671 DOI: 10.1039/J39680002671
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