Hydrochloric Acid → 5-Dodecylthiophene-2-carboxylic acid

Participants

Reaction Steps

In a 2 liter-four-necked flask, 30.0 g (1.07×10-1 mol) of 5-dodecylthiophene-2-carbaldehyde, 6.0 g of NaOH, 21.3 g of KMnO4 and 900 ml of water were placed and stirred for 17 hours at room temperature. After the reaction, the reaction mixture was acidified with conc. hydrochloric acid, followed by four times of extraction with 300 ml of ethyl acetate, three times of washing with 500 ml of water, drying with anhydrous magnesium sulfate and distilling-off of the solvent to obtain 29.9 g of a crude product. The crude product was purified by silica gel column chromatography with the use of an hexane/ethyl acetate (=2/1) mixture solvent and recrystallized from ethyl acetate to obtain 12.1 g of a pure product (yield: 38.2%).

Provenance & Evidence