2-Furanacrylic Acid

  • A. L. Mndzhoian


A mixture of 192 g (2 moles) of freshly distilled 2-furaldehyde, 208 g (2 moles) of malonic acid, dried at 100°, and 96 ml (1.2 moles) of pyridine, dried over potassium hydroxide, was prepared in a one-liter round-bottomed flask fitted with reflux condenser. The mixture was heated for two hours in a boiling water bath; it was then cooled to room temperature, and 200 ml of water was added. Concentrated aqueous ammonia was then added to the stirred mixture until the acid had almost dissolved; the solution was filtered, and the filter was washed with a little water. The solution was acidified to Congo red with dilute hydrochloric acid and left for 1.5–2 hours in an ice bath. The precipitated 2-furanacrylic acid was filtered off, washed with three 80-ml portions of water, and dried in a desiccator over calcium chloride. The product, which amounted to 252–254 g (91–92%), consisted of colorless needles, m.p. 141° (see Notes).


Acrylic Acid Glacial Acetic Acid Calcium Chloride Sodium Acetate Potassium Hydroxide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature Cited

  1. 1.
    J. G. Schmidt, Ber. 13, 2344 (1880); Swedish Pat. 118, 461 (1947) [C.A. 42, 223d (1948)]Google Scholar
  2. A. Scipioni, Chim. e ind. (Milan) 34, 78 (1952) [C.A. 46, 7813b (1952)].Google Scholar
  3. 2.
    C. D. Hurd and C. L. Thomas, J. Am. Chem. Soc. 55, 1646 (1933)Google Scholar
  4. M. E. Egorova and M. A. Abramova, Zh. priklad. khim. (J. Appl. Chem.) 23, 1311 (1950).Google Scholar
  5. 3.
    A. Bayer, Ber. 10, 357 (1877)Google Scholar
  6. W. Marckwald, Ber. 20, 2812 (1887)Google Scholar
  7. Gibson and Kahnweiler, Am. Chem. J. 12, 314 (1890)Google Scholar
  8. M. M. Koton, A. P. Votinova, and F. S. Florinskii, Zh. priklad. khim. (J. Appl. Chem.) 14, 181 (1941)Google Scholar
  9. L. Galimberti, Boll. sci. facolta chim. in Bologna 351 (1940) [C.A. 37, 34102 (1943)]Google Scholar
  10. A. Mora and J. Infiesta, Combustibles (Zaragoza) 7, No. 37, 27 (1947) [C.A. 42, 8519g (1948)]Google Scholar
  11. Y. Hachihama, M. Imoto, and K. Kawata, J. Soc. Chem. hid. Japan 45, Suppl., 189 (1942) [C.A. 44, 9721e (1950)].Google Scholar
  12. 4.
    A. Scipioni and V. Borsetto, Ann. Chim. (Rome) 42, 185 (1952) [CA. 47, 3293h (1953)]Google Scholar
  13. A. M. Shur and A. I. Moiseenko, Zh. priklad. khim. (J. Appl. Chem.) 27, 405 (1954).Google Scholar
  14. 5.
    S. Matura, K. Endo, and K. Ota, Bull. Nat. Hyg. Lab. (Japan) 67, 157 (1950).Google Scholar
  15. 6.
    E. Knoevenagel, Ber. 31, 2614 (1898).Google Scholar
  16. 7.
    S. Dutt, Quart. J. Chem. Soc. 1, 297 (1925) [C.A. 19, 24754 (1925)]Google Scholar
  17. P. N. Kurien, K. C. Pandya, and V. R. Surange, J. Indian Chem. Soc. 11, 823 (1934) [C.A. 29, 33255 (1935)].Google Scholar
  18. 8.
    S. Rajagopalan, Proc. Indian Acad. Sci. 16A, 163 (1942) [C.A. 3–7, 14233 (1943)]Google Scholar
  19. S. Rajagopalan and P. V. A. Raman, Organic Syntheses (Russian Translation), Vol. 3, p. 456, Foreign Lit. Press, Moscow, 1952 [Organic Syntheses, Collective Vol. 3, New York and London, 1955, p. 425].Google Scholar

Copyright information

© Springer Science+Business Media New York 1959

Authors and Affiliations

  • A. L. Mndzhoian

There are no affiliations available

Personalised recommendations