Journal of Chemical Research

Convenient syntheses of m-and p-ethynylphenols

GQ Lai, SL Liu, JF Xu, YJ Shen

Index: Lai, Guo-Qiao; Liu, Shi-Ling; Xu, Jin-Feng; Shen, Yong-Jia Journal of Chemical Research, 2006 , # 3 p. 203 - 204

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Abstract

m-Iodophenol (4a) was found to couple with 2-methylbut-3-yn-2-ol (5) in the presence of PdCl2-CuI-Ph3P-in triethyl-amine to afford 3-(3-hydroxy-3-methylbut-1-ynyl) phenol (6a), which was conveniently converted into m-ethynylphenol (7a). Under the same conditions, p- iodophenol did not couple with 5. However, p-iodo-1-[(tetrahydro-2H-pyran-2-yl) oxy] benzene (4b) did react with 5 to afford 1-[(tetrahydro-2H-pyran-2-yl) oxy]-4-[2-hydroxy-2- ...