Sulfuric Acid → Perfluoro-2-[3-(methoxy)propoxy]acetic acid

Participants

Reaction Steps

5.5 mL water, 16 ml MeCN, 0.32 g KBr, TEMPO (0.11 g), and 8 g of 2,2-difluoro-2-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxy-propoxy)-ethanol are placed in a 100 ml glass flask equipped with a dropping funnel and stirrer. 43 mL of 15% (wt) aq. NaOCl buffered to pH 8-9 were added via the dropping funnel in 3 portions over two days while stirring at room temperature. Concentrated sulphuric acid and water were added to bring the pH to about 1 to 2. The reaction mixture was extracted three times by diethyl ether and the combined ether phases were dried over magnesium sulphate. The solvent was evaporated to give colorless liquid, which was distilled using a water pump (15 mmHg, 70° C.) to give 7.25 g of the acid. Yield: 87%. 1H NMR (CDCl3): 9.39 (s, 1H); 19F NMR (CDCl3): −56.28 (t, J=8.7 Hz, 3F); −79.19 (t, J=11.9 Hz, 2F); −84.58 (m, 2F); −86.86 (m, 2F); −130.45 (m, 2F).

Provenance & Evidence