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

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.

1. temperaturethe reaction mixture was then maintained
2. temperatureThe reaction mixture was then maintained overnight
3. stirringwith stirring, at ambient temperature
4. customThe solvent was removed by evaporation under reduced pressure (water-pump)
5. customthe crystalline residue was partitioned between diethyl ether (670 ml) and water (200 ml)
6. customThe ether layer was separated
7. washwashed with water (2×200 ml)
8. dry with materialdried over anhydrous sodium sulphate
9. customevaporated under reduced pressure (water-pump)
10. customThe solid residue thus obtained
11. distillationwas distilled

ORD record

ord-fbf7479b2e2f4b2195617b9ba5d7977e

Source dataset

uspto-grants-1982_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04347252