Methyl perfluorohexanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1 mole each of C5F11COOCH3 (made by electrofluorination of hexanoyl chloride and subsequent reaction with methanol, 82 percent linear C5F11) and NH2C2H4OH was heated in methanol (about 200 mL) for 18 hours at 55-60° C. and stripped to provide 355.3 g C5F11CONHC2H4OH, 100 g of which was treated cautiously with 25 mL SOCl2 (obtained from Aldrich Chemical Company, Milwaukee, Wis.), heated for 18 hours at 55-60° C., and stripped to provide 102.1 g C5F11CONHC2H4Cl, 37.5 g of which was dissolved in 100 mL methanol and treated with 6.0 g powdered NaOH. After stirring the resulting mixture for 20 hours at 23° C., the mixture was quenched in water, extracted with dichloromethane, and dried over MgSO4. Distillation of the dried mixture yielded 15.0 g pure C5F11-oxazoline as a colorless liquid (boiling point 170° C.).