Preparation of Perfluorocarboxylic Acids from Esters by Electrochemical Fluorination

Electrochemical fluorination of several esters derived from oxolane-2-yl-carboxylic acid, oxolane-2-yl-methanol and oxane-2-yl-methanol

“…Oxolane-2-yl-carbonyl chloride (6) was prepared by the Scheme 5. reaction of thionyl chloride and oxolane-2-yl-carboxylic acid (1) (Wako Chemicals Co.). Methyl oxolane-2-ylcarboxylate (7) and oxolane-2-yl-methyl oxolane-2-ylcarboxylate (8) was prepared by the reaction of 6 with methanol and 2, respectively. Oxane-2-yl-methyl acetate (11) was prepared by the reaction of acetyl chloride (Wako Chemicals Co.) and oxane-2-yl-methanol (3) (Tokyo Kasei Co.).…”

“…We have investigated the preparation of perfluoro-(oxolane-2-yl-carbonylfluoride) (4) by the electrochemical fluorination (ECF) of the following samples: oxolane-2-ylcarbonyl chloride (6), methyl oxolane-2-yl-carboxylate (7), oxolane-2-yl-methyl oxolane-2-yl-carboxylate (8), oxolane-2-yl-methanol (2), oxolane-2-yl-methyl acetate (9) and oxolane-2-yl-methyl trifluoroacetate (10). Furthermore, ECF of acetates of oxane-2-yl-methanol [acetate (11), trifluoroacetate (12)] was investigated to obtain perfluoro-(oxane-2-yl-carbonylfluoride) (5).…”

“…Next, the ECF of derivatives of oxolane-2-yl-methanol (2) was examined, as it is known that primary alcohol could serve as starting materials for perfluoroacid fluoride on ECF [8][9][10][11]. When 2 was subjected to ECF, the target 4 was obtained in 6% yield.…”