Derivatives. Ethers derived from Alkenylphenols

4-(But-2-enyl)phenol readily formed an allyl ether in quantitative yield when its sodium salt was reacted with allyl chloride. This compound underwent Claisen rearrangement at 200°C to afford 2-allyl-4-but-2-enylphenol, the allyl ether of which, in turn, was rearranged to give 2,6-diallyl-4-but-2-enylphenol. Selective isomerisation of the allyl groups of this compound took place by heating at 110°C to afford 2,6-dipropenyl-4-but-2-enylphenol (ref.102). 

Al-Saati, T.N. Chernysheva and V.A. Vinokurov, lonnyi Obmen lonity, Leningrad, 1970, 310. 

Fujimoto, Y. Shibahara and Y. Shimoyama (Sanyo Chem. Industry 

Tsuzki and K. Komiya, (Asahi Denka Kogyo KK, Eur. Pat. Appin., EP 458634). 

Gorecki, M. Lewandowski, K. Grabas, Helena Gorecki, J. Hoffmann, 

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Pathway G Synthesis of 2-(l-hydroxyalkyl)benzofuran derivatives from o-alkenylphenols. o-Allylphenols and their benzyl ethers (168), treated with a peroxy acid, give epoxides which, according to conditions, lead... 

Some of this group are listed in Table 13.3 All the members are 3-alkenylphenols sometimes, as with campnospermanol, containing a keto function in the side chain. The highly unsaturated substance flexirubin is a phenolic ester from a bacterial source. Complex phenolic ether compounds, essentially 0-glycosyl derivatives of c6-(4-hydroxyphenyl)phthiocerol A have been isolated from mycobacterial sources (ref. 75). 

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