Water → HCID 19849494, compound

Participants

Reaction Steps

To a solution of 2.35 g (0.025 mol) of phenol in 20 ml of absolute ethanol, there was added 1.10 g (0.0275 mol) of sodium hydroxide. The mixture was refluxed until complete disolution and 2.92 g (0.0125 mol) of 1-bromobut-2-yn-4-ol tetrahydropyranyl ether were added, and the reflux resumed for 2 additional hours. It was then cooled, poured into water and extracted with ether. The organic extracts were washed with 20% aqueous sodium hydroxide solution and water, dried 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-phenoxybut-2-yn-1-ol tetrahydropyranyl ether, as an oil.

Provenance & Evidence