2,2,2-Trifluoroethanol → 2,2,2-Trifluoroethyl 2-naphthalenesulfonate

Participants

Reaction Steps

To a stirred solution of 25.0 parts of 2,2,2-trifluoroethanol in 175 parts of N,N-diethylethanamine were added portionwise 62.2 parts of 2-naphthalenesulfonyl chloride. Upon completion, a mixture of 1.5 parts of N,N-dimethyl-4-pyridinamine and 25 parts of ethyl acetate was added during a period of 20 minutes. Upon complete addition, stirring was continued overnight at room temperature. The reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was stirred in water and solidified product was filtered off under reduced pressure. The precipitated product was dissolved in dichloromethane. The organic layer was dried, filtered and evaporated in vacuo. The residue was treated with petroleum ether. After filtration, the precipitated product was crystallized from 2-propanol. The product was filtered off and dried, yielding 65.3 parts (89%) of 2,2,2-trifluoroethyl 2-naphthalenesulfonate; mp. 72.7° C. (int. 36).

Provenance & Evidence