Methanol → 2,3,3,3-Tetrafluoro-2-methoxypropanoic acid

Participants

Reaction Steps

The synthesis of Example 9 was carried out under pressure as follows. A 100 ml stainless steel stirred reactor chilled to 0° was charged with 32.8 g of aqueous sodium hydroxide solution and 50.1 g of methanol. The reactor was cooled to -78° and 23.7 g (0.143 mol) of hexafluoropropene epoxide was condensed therein. The cooling bath was removed, and stirring was started. The reaction temperature rose to 50°, and the pressure to 185 psig. The reaction was completed in an hour, but stirring was continued for another hour. The reaction mixture was neutralized by 3 g of 50% aqueous sodium hydroxide solution. The low boilers were removed by evaporation, and the resulting white solid (40.6 g) was combined with 40.7 g of 99% phosphoric acid and distilled to afford 17.1 g (67.9%) of 2-methoxytetrafluoropropionic acid (1H NMR) b.p. 55°-60° (7 mm Hg).

Provenance & Evidence