
%0 Journal Article
%A Hlubucek, J 
%A Ritchie, E 
%A Taylor, WC 
%T Synthesis of o-isopentenylphenols
%J Australian Journal of Chemistry
%D 1971/11/01
%V 24
%N 11
%P 2355-2363
%K 
%R https://doi.org/10.1071/CH9712355
%U https://www.publish.csiro.au/paper/CH9712355 
%X The effect of the solvent and the counter-ion on the ring alkylation of 3- and 4-methoxyphenols by isopentenyl bromide has been examined. Under strictly anhydrous conditions good and consistent yields of the o- isopentenylphenols were obtained with the combination potassium- toluene, but sodium-toluene was more convenient.     Boron trifluoride etherate was more satisfactory than stannic chloride, zinc chloride, or phosphoric acid in catalysing the condensation of 3- and 4-methoxy-phenols with 2-methylbut-3-en-2-ol to the corresponding o-isopentenylphenols. Aryl &#945;,&#945;-dimethylpropargyl ethers were partially hydrogenated to the corresponding &#945;,&#945;- dimethylallyl ethers which rearranged in boiling N,N-diethyl-aniline to o-isopentenylphenols in high overall yield. 
