Toluene → 2,2,2-Trifluoroethanol

Participants

Reaction Conditions

Reaction Steps

Aluminum trifluoroethoxide was prepared by treatment of a toluene solution of triethylaluminum (0.38M) with these equivalents of trifluoroethanol at -25° C. After gas evolution was complete, the reaction mixture was allowed to stand at room temperature. When precipitation of product appeared to be well-advanced (1-2 hr), the reaction mixture was cooled at -25° C. for 18 hr before collecting the solid product. From 1.76 mmol of Et3Al and 0.528 g trifluoroethanol was obtained 435 mg of white solid, mp 171°-172° C. 1H NMR (THF-d8): 4.1 (q, J=8). 19F NMR (THF-d8): -77.0 (bd s), trace signals at -76.3 and-77.7.

Provenance & Evidence