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Original scientific paper

Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde

Jaroslav Horvat ; »Ruđer Bošković« Institute, Department of Organic Chemistry and Biochemistry, 41001 Zagreb, P. O. B. 1016, Yugoslavia
Branimir Klaić ; »Ruđer Bošković« Institute, Department of Organic Chemistry and Biochemistry, 41001 Zagreb, P. O. B. 1016, Yugoslavia
Biserka Metelko ; »Ruđer Bošković« Institute, Department of Organic Chemistry and Biochemistry, 41001 Zagreb, P. O. B. 1016, Yugoslavia
Vitomir Šunjić ; »Ruđer Bošković« Institute, Department of Organic Chemistry and Biochemistry, 41001 Zagreb, P. O. B. 1016, Yugoslavia

Fulltext: english, pdf (6 MB) pages 429-438 downloads: 167* cite
APA 6th Edition
Horvat, J., Klaić, B., Metelko, B. & Šunjić, V. (1986). Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde. Croatica Chemica Acta, 59 (2), 429-438. Retrieved from https://hrcak.srce.hr/177372
MLA 8th Edition
Horvat, Jaroslav, et al. "Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde." Croatica Chemica Acta, vol. 59, no. 2, 1986, pp. 429-438. https://hrcak.srce.hr/177372. Accessed 19 Apr. 2021.
Chicago 17th Edition
Horvat, Jaroslav, Branimir Klaić, Biserka Metelko and Vitomir Šunjić. "Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde." Croatica Chemica Acta 59, no. 2 (1986): 429-438. https://hrcak.srce.hr/177372
Harvard
Horvat, J., et al. (1986). 'Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde', Croatica Chemica Acta, 59(2), pp. 429-438. Available at: https://hrcak.srce.hr/177372 (Accessed 19 April 2021)
Vancouver
Horvat J, Klaić B, Metelko B, Šunjić V. Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde. Croatica Chemica Acta [Internet]. 1986 [cited 2021 April 19];59(2):429-438. Available from: https://hrcak.srce.hr/177372
IEEE
J. Horvat, B. Klaić, B. Metelko and V. Šunjić, "Mechanism of Levulinic Acid Formation in Acid Catalysed Hydrolysis of 2-Hydroxymethylfurane and 5-Hydroxymethylfurane- 2-carhaldehyde", Croatica Chemica Acta, vol.59, no. 2, pp. 429-438, 1986. [Online]. Available: https://hrcak.srce.hr/177372. [Accessed: 19 April 2021]

Abstracts
Mechanism of levulinic acid (2) formation in acid catalysed hydrolysis of 2-hydroxymethyl£urane (3) and 5-hydroxymethylfuran- 2-carbaldehyde (1) is studied by 13C-NMR spectroscopy. Hydroxymethyl-derivative of dihydrofurane 5, its anhydro-derivative
6, and an unsaturated keto-aldehyde (8) are determined as intermediates in the transformation of 3 into 2 (Scheme 3). The conversion of 1 into 2 requires more drastic conditions, and
the only two structures determined unambigously are 15 and 16;
the former intermediate led to polymerized material via A-5,
analogous to polymerization of 4 via 13 and 14 (Scheme 4), while
the latter decarbonylates and rearranges to afford levulinic acid
(Scheme 5). Intramolecular oxygen transfer via cyclic intermediates
(Scheme 6), embracing concerted C(l)-O and C(5)-X (X = H or eHO) bond breaking, cannot be proved.

Hrčak ID: 177372

URI
https://hrcak.srce.hr/177372

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