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Laevulinic Acid

LAEVULINIC ACID (/3-acetopropionic acid), C 5 H 8 O 3 or CHsCO-CHi-CHfCOifl, a ketonic acid prepared from laevulose, inulin, starch, etc., by boiling them with dilute hydrochloric or sulphuric acids. It may be synthesized by condensing sodium acetoacetate with monochloracetic ester, the acetosuccinic ester produced being then hydrolysed with dilute hydrochloric acid (M. Conrad, Ann., 1877, 188, p. 222). CHj-CO-CH-Na CH,-COCH-CH 2 -CO 2 R ! -> I ->CH 3 COCH 2 -CH 2 -CO 2 OH.

CO 2 R CO 2 R It may also be prepared by heating the anhydride of 7- methyloxyglutaric acid with concentrated sulphuric acid, and by oxidation of methyl heptenone and of geraniol. It crystallizes in plates, which melt at 32-5-33 C. and boil at 148-149 (15 mm.) (A. Michael, Jour. prak. Chem., 1891 [2], 44, p. 114). It is readily soluble in alcohol, ether and water. The acid, when distilled slowly, is decomposed and yields a and ^-angelica lactones. When heated with hydriodic acid and phosphorus, it yields -valeric acid; and with iodine and caustic soda solution it gives iodoform, even in the cold. With hydroxylamine it yields an oxime, which by the action of concentrated sulphuric acid rearranges itself to N-methylsuccinimide [CHz-COLN-CHi.

Note - this article incorporates content from Encyclopaedia Britannica, Eleventh Edition, (1910-1911)

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