Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-Phenoxybut-2-yn-1-ol

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Reaction Conditions

Reaction Steps

1.02 g (0.004 mol) of pyridinium p-toluenesulfonate was added to a solution of 2 g of 4-phenoxy-but-2-yn-1-ol tetrahydropyranyl ether in 20 ml of 96% ethanol. The reaction mixture was stirred for 2 hours at 55° C.; the solvent was then removed in vacuo and the residue diluted with 20 ml of water and extracted with methylene chloride (3×20 ml). The combined extracts were dried over sodium sulfate and the solvent evaporated in vacuo. The residue was purified by column chromatography on 30 g of silica gel, using hexane-ethyl acetate (90:10) as eluant, to yield 4-phenoxy-but-2-yn-1-ol, as an oil.

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