4297. 2-Furanacrylic Acid

Nomenclature

CAS number: 539-47-9
3-(2-Furanyl)-2-propenoic acid; β-2-furylacrylic acid; furacrylic acid; 2-furalacetic acid; furfurylidene acetic acid.
C7H6O3; mol wt 138.12.
C 60.87%, H 4.38%, O 34.75%.

Description and references

Prepd by the condensation of furfural with malonic acid in the presence of pyridine. Laboratory procedure: S. Rajagopalan, P. V. A. Raman, Org. Synth. 25, 51 (1945). Large scale procedure: Johnson, ibid. 20, 55 (1940). Acid dissociation determn: C. C. Price, E. A. Dudley, J. Am. Chem. Soc. 78, 68 (1956).

Chemical structure

Properties

Colorless needles from water, mp 141°. Sublimes in high vacuum at 112°. bp760 286°; also reported as bp760 226°; bp8 117°. pKa in ethanol (25°): 6.49. Volatile in steam. One gram dissolves in 500 ml water at 15°. 100 ml of a satd benzene soln contains 1.14 g at 19°. Sol in alcohol, ether, glacial acetic acid.

Derivative

Labile Form.

Properties

mp 104°. Can be converted to the stable form by exposure to sunlight in benzene soln contg some iodine.