Synthesis and identification of 3,5-bis(hydroxymethyl)tetrahydro-4H-pyran-4-one

Keywords: tetrahydropyranone, acetone, formaldehyde, synthesis, condensation, conformational analysis, quantum-chemical calculations, Gaussian


3,5-bis(hydroxymethyl)tetrahydro-4H-pyran-4-one by condensation of acetone with formaldehyde in the ratio of 1:4 in an alkaline medium at a temperature of 30-35°С (product yield 67.4%) was obtained. To determine the composition of obtained compound elemental analysis was used. Functional composition and structural elements were identified using IR spectroscopy. To prove the structure of the synthesized compound, 1H and 13C NMR spectra were taken on a JNN-ECA Jeol 400 spectrometer (at a frequency of 399.78 MHz and 100.53 MHz) with a CDCl3 solvent. Quantum-chemical calculations of stable conformations of 3,5-bis(hydroxymethyl)tetrahydro-4H-pyran-4-one was performed using ab initio DFT B3LYP method and 6-31G (d) and 6-311+G(3df,2p) basis sets. It was found that the stable conformers obtained by calculations are in the "chair" conformation; the hydroxymethyl substituents in conformer I are located equatorially, in conformation II – axially and equatorially, in conformation III – axially. In the conformer III, as a result of spatial proximity, hydroxymethyl substituents form an intramolecular hydrogen bond. The total energies and dipole moments were calculated; a lower value of the dipole moment of the conformation II may indicate its preference over the others.


1 Wang J, Sun G, Li Z, Mai W, Xie J (2012) Journal of Chemical Research 36:63-65. Crossref

2 Makarov MV, Leonova ES, Rybalkina EY, Khrustalev VN, Shepel NE, et al (2012) Arch Pharm 345:349-359. Crossref

3 Nottelet B, Patterer M, François B, Schott MA, Domurado M, et al (2012) Biomacromolecules 13:1544-1553. Crossref

4 Kandhare AD, Raygude KS, Ghosh P, Ghule AE, Bodhankar SL (2012) Fitoterapia 83:650-659. Crossref

5 Petrov GS, Rutovskii BN, Losev IP (1946) The technology of synthetic resins and plastics [Tehnologiya sinteticheskih smol i plasticheskih mass]. Goskhimizdat, Moscow, Russia. (In Russian)

6 Morgan GT, Holmes EL (1932) J Chem Soc 1:2612-2620. Crossref

7 Zubkov FI, Nikitina EV, Zaytsev VP, Khrustalev VN, Novikov RA, et al (2012) Chem Heterocycl Compd 5:785-794. Crossref

8 Mistryukov ÉA (1965) B Acad Sci USSR Ch+ 14:1793-1796. Crossref

9 Diwischek F, Arnone M, Engels B, Holzgrabe U (2005) Tetrahedron 61:6993-7001. Crossref

10 Miranda MS, Da Silva JCGE, Hon C, McKerrall SJ, Liebman JF (2013) Struct Chem 24:1829-1839. Crossref

11 Bauenov KH, Sarieva ShA (2018) Synthesis of novel tetrahydropyronone and its derivatives [Jańa tetragıdropıranon men onyń keıbіr týyndylaryn sıntezdeý]. Abstracts of the International Conference of Students and Young Scientists «Farabı Álemі». Almaty, Kazakhstan P.49. (In Kazakh)
How to Cite
Bazhykova, K., Langer, P., Yergaliyeva, E., Seylkhanov, T., & Abilov, Z. (2018). Synthesis and identification of 3,5-bis(hydroxymethyl)tetrahydro-4H-pyran-4-one. Chemical Bulletin of Kazakh National University, 91(4), 4-9.