Sulfuric Acid → 2-Methyl-2-(2,2,2-trifluoroethoxy)propane

Participants

Reaction Conditions

Reaction Steps

Approximately 55 g (0.55 mol) trifluoroethanol and 2 g concentrated sulfuric acid were placed in a 300 ml glass pressure bottle equipped with a magnetic stir bar and pressure gauge. The pressure bottle was evacuated briefly and the stirred contents were cooled in a water bath at about 20° C. in order to moderate the temperature of the somewhat exothermic reaction with isobutylene. Isobutylene was then added to a pressure of about 20 psig. The isobutylene supply was turned off and the reaction was monitored by the decrease in pressure in the glass reactor. After the pressure had fallen to 0 psig, additional isobutylene was charged. In this manner, a total of 20.1 g (0.359 mol) isobutylene was added. The mixture was then poured into 300 ml of cold water and extracted with 50 ml of dodecane. The organic layer was separated, washed with three (3) 50 ml portions of water and dried over anhydrous powdered magnesium sulfate. The organic layer was distilled affording 28.5 g (51%) tertiary butyl 2,2,2-trifluoroethyl ether, bp 82.5°-84° C. 1H NMR (CDCl3): δ 3.77 (q, 2H, J=8 Hz), 1.25 (s, 9 H).

Provenance & Evidence