[OH-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][CH2:17][C:18]#[C:19][CH2:20]Br.O>C(O)C>[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][CH2:17][C:18]#[C:19][CH2:20][O:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=11.10 g of sodium hydroxide was added to a solution of 2.35 g of phenol in 20 ml of absolute ethanol. The mixture was refluxed until complete dissolution, then 2.92 g of 1-bromobut-2-yn-4-ol tetrahydropyranyl ether was added. The reflux was resumed for 2 additional hours. It was then cooled, poured into water and extracted with ether (3×50 ml). The organic extracts were washed with 20% aqueous sodium hydroxide solution and water, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on 50 g of silica gel, using hexane:ethyl acetate (98:2) as eluant, to yield 4-phenoxy-but-2-yn-1-ol tetrahydropyranyl ether, as an oil.
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