Propargyl alcohol → 3-[3,5-Bis(trifluoromethyl)phenyl]prop-2-yn-1-ol

Participants

Reaction Steps

To a stirred solution of 3,5-bistrifluoromethyliodobenzene (which may be prepared as described by S. D. Ross et al, J. Amer. Chem. Soc. (1953), 75, 4967-4969; 340.1 g) in anhydrous diethylamine (665 ml), cooled to 10° C. and under an inert atmosphere, there were added successively copper (I) iodide (1.81 g) and dichlorobis(triphenylphosphine)palladium (3.51 g). 2-Propyn-1-ol (57.8 g) was then added dropwise over 20 minutes and the reaction mixture was then maintained, with stirring, at 25° to 30° C. for 4 hours. The reaction mixture was then maintained overnight, with stirring, at ambient temperature. The solvent was removed by evaporation under reduced pressure (water-pump) and the crystalline residue was partitioned between diethyl ether (670 ml) and water (200 ml). The ether layer was separated, washed with water (2×200 ml), dried over anhydrous sodium sulphate and evaporated under reduced pressure (water-pump). The solid residue thus obtained was distilled to give 1-(3,5-bistrifluoromethylphenyl)-prop-1-yn-3-ol, in the form of a white crystalline solid (231.7 g), m.p. 58°-60° C., b.p. 87°-91° C./1 mm Hg.

Provenance & Evidence