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

Temperature

20 °C

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).

1. customequipped with a magnetic stir bar
2. customThe pressure bottle was evacuated briefly
3. customthe temperature of the somewhat exothermic reaction with isobutylene
4. additionwas charged
5. extractionextracted with 50 ml of dodecane
6. customThe organic layer was separated
7. washwashed with three (3) 50 ml portions of water
8. dry with materialdried over anhydrous powdered magnesium sulfate
9. distillationThe organic layer was distilled

ORD record

ord-7c53d3da8bfe49bea6e06ea8e4b7099e

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05091104