Sulfuric Acid → 4,4,5,5,5-Pentafluoropentyl 4-methylbenzenesulfonate

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Reaction Conditions

Reaction Steps

A solution of 17.3 g of 4,4,5,5,5-pentafluoropentanol in 40 ml of pyridine is mixed at 0° C. with 21 g of tosyl chloride and stirred for 3 hours at 0° C. For working up, the reaction mixture is added to 2 n sulfuric acid, extracted with diethyl ether, washed neutral with water, dried on sodium sulfate and concentrated by evaporation in a vacuum. 32.7 g of crude toluene-4-sulfonic acid-4,4,5,5,5-pentafluoropentyl ester is obtained as oil. The latter is dissolved in 300 ml of acetone and refluxed with 23 g of potassium thioacetate for 18 hours at 100° C. bath temperature. Then, it is mixed with water, extracted with diethyl ether, washed with water, dried on sodium sulfate, concentrated by evaporation in a vacuum and distilled. At 173°-177° C., 15 g of thioacetic acid-S-(4,4,5,5,5-pentafluoropentyl)-ester is obtained.

Provenance & Evidence