Sulfuric Acid → ADONA

Participants

Reaction Steps

5.5 mL water, 20 mL MeCN, 0.36 g KBr, 4-MeOTEMPO (0.15 g), and 10 g of 2,2,3-trifluoro-3-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxy-propoxy)-propan-1-ol are placed in a 50 ml glass flask equipped with a dropping funnel and stirrer. 36 mL of a 15% wt. aq. NaOCl solution 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 make the reaction mixture acidic (pH 1 to 2). The reaction mixture was extracted three times with diethyl ether. The combined ether phases were dried over magnesium sulphate and the solvent was removed by a rotary evaporator. The residue was distilled to give 8.4 g of the acid (b.p. 58 C, 1.6 mmHg). Yield: 81%.

Provenance & Evidence