Chloroacetic Acid → 2-Thiopheneacetic acid

Participants

Reaction Steps

Aqueous solution of sodium hydroxide 8.8 g (0.22 mol) in water of 15 ml was added drop by drop to mixture of 2-mercapto furan 20.0 g (0.20 mol), chloroacetic acid 27.0 g (0.22 mol) and ethanol 300 ml with stirring at room temperature. After 20 minutes of stirring it was heated to 50° C., and further aqueous solution of sodium hydroxide 8.8 g (0.22 mol) in 15 ml of water was added slowly drop by drop. After stirring for 3 hours at 50° C., it was cooled to room temperature, and water was added till reaction liquid became uniform. Hydrochloric acid was added for neutralization. Prepared crystal was collected by filtration and 23.5 g (0.148 mol) of 2-carboxymethylthiofuran was obtained by recrystallization in methanol. Synthesis of yield 74%.

Provenance & Evidence