Propargyl alcohol → 3-Pentadecyl-1-(2-propynyloxy)benzene

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To a solution of 24.4 g (80 mmol) of 3-pentadecylphenol, 4.93 g (88 mmol) of propargyl alcohol and 23.1 g (88 mmol) of triphenylphosphine cooled to 15° C. is added dropwise 15.3 g (13.9 ml, 88 mmol) of diethyl azodicarboxylate. The mixture is stirred for 4.5 hours and then is diluted with water and extracted with hexane (3 times). The hexane extracts are combined, washed with 1N sodium hydroxide and are dried over magnesium sulfate overnight. Filtration and evaporation gives crude oil which is subjected to flash chromatography using hexane as eluting solvent. The appropriate fractions are combined to give the title compound as an oil which solidifies upon standing: mp. 26°-27° C. The product is used without further characterization.

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