Sodium Hydroxide → 1H-Perfluorooct-1-yne

Participants

Reaction Conditions

Reaction Steps

A flame-dried 50 mL round-bottom flask equipped with distillation apparatus was charged with 5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluoro-2-methyldec-3-yn-2-ol (S1) (35.3 g, 88 mmol) and NaOH pellets (2.5 g, 61 mmol) under argon. The pressure was reduced to 400 mmHg and the flask was heated to 100° C. The crude product was collected over an hour in a receiving flask in a brine/ice bath. The product was washed 3 times with distilled water and was subsequently dried over MgSO4. Removal of drying agent via filtration gave S2 (13.4 g, 46%) as a clear liquid. B.p. 92-94° C. 1H NMR (300 MHz, CDCl3): δ 3.07 (t, JH-F=5.7 Hz, 1H). 19F NMR (282 MHz, CDCl3): δ −126.69 (2F), −123.39 (2F), −123.25 (2F), −121.83 (2F), −99.76 (2F), −81.33 (3F).

Provenance & Evidence