Hydrochloric Acid → 1,1,1,5,5,5-Hexafluoropentan-3-one

Participants

Reaction Steps

A mixture of 20 mL 100% H2SO4, 10.6 g (0.049 mol) HgO; and 12.0 g (0.048 mol) CF3CH2CCl2CH2CF3 was shaken periodically over 45 min, during which time a thick, nearly white paste resulted. An exothermic reaction also occurred after approximately 10 min and subsided after about 0.5 h. The cooled reaction mixture was added to 75 g ice and 25 mL concentrated HCl. The lower liquid phase was separated and the aqueous layer was extracted with 3×35 mL ether. The combined organic extracts (including the original organic layer) were washed with 10 mL water, dried with Na2SO4 and distilled. Five and three tenths g (56% yield) of 97% pure CF3CH2C(O)CH2CF3 were obtained (boiling point 122-123° C.). 1H NMR: 3.4 (q, J=10.2 Hz). 19F NMR: -63.0 (t, J=10.2 Hz) ppm. IR: 1746 (C=O) cmc-1. MS: 194 (3.4), 111 (100), 91 (17.5), 83 (21.8), 69 (11.9).

Provenance & Evidence