furan-2-acetic acid

Uses

2-(Furan-2-yl)acetic Acid is one of the compounds detected in tobacco smoke condensate.

Definition

ChEBI: 2-furanacetic acid is a heteroarene.

Synthesis

The general procedure for the synthesis of 2-furanacetic acid from 2-(furan-2-yl)acetonitrile was as follows: to a solvent mixture of 30 mL of 3N sodium hydroxide solution and 30 mL of methanol, 3.34 g (31.2 mmol) of 2-(furan-2-yl)acetonitrile was added, and stirred until it was completely dissolved. The reaction mixture was heated to reflux for 2 hours and 30 minutes with continuous stirring. After completion of the reaction, the solution was cooled to room temperature and separated by extraction with ether. The aqueous phase was acidified with 20 mL of concentrated hydrochloric acid to release the organic products and extracted again with ether. The ether extracts were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give 3.84 g (30.5 mmol) of 2-furanacetic acid in 97.8% yield.

References

[1] Patent: US6215016, 2001, B1
[2] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1993, # 10, p. 1941 - 1946
[3] Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 5, p. 1361 - 1365
[4] Chemische Berichte, 1930, vol. 63, p. 749,753
[5] Journal of the American Chemical Society, 1930, vol. 52, p. 1284