Oxygen → 2,2,3,4,4-Pentafluoro-4-[1,1,2,2,3,3-hexafluoro-3-(trifluoromethoxy)propoxy]butanoic acid

Participants

Reaction Conditions

Reaction Steps

80 mL of acetic acid, 0.32 g sodium nitrite, TEMPO (0.24 g), CH3CO2Na (1.13 g) and 8 g of 2,2,3,4,4-pentafluoro-4-(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxy-propoxy)-butan-1-ol were placed in a 200 mL glass flask equipped with a balloon containing molecular oxygen, a reflux condenser and a stirrer. The balloon was opened such that a gentle flow of oxygen was generated. The mixture was stirred for 16 hr at 60° C. upon which the mixture was acidified to pH 1 to 2 and extracted with diethyl ether (three times). The combined organic phases were washed with water and dried over magnesium sulphate. The solvent was removed at a rotary evaporator and the residue was distilled to give 5.89 g of acid (1.6 mmHg, 65° C.). Yield: 71%.

Provenance & Evidence