SYNTHESIS OF UNSATURATED SPIROACETALS, CYCLOPENTANONE DERIVATIVES
607
decrease in the acetal yield by 12%, a change that is
due to an increase in the rate of further transforma-
tions of the forming acetals to polyoxy compounds and
dehydration of glycol to dioxane.
REFERENCES
1. S. Yu. Shavshukova, I. N. Vikhoreva, and E. A. Uda-
lova, Bashkir. Khim. Zh. 16, 123 (2009).
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3. O. Okaoda and K. Mita, Makromol. Chem. 176, 859
The results of the experiments on the condensation
of 2-pentylidenecyclopentanone with ethylene glycol
are presented in Table 2.
(1975).
4. S. A. Voitkevich, 865 Fragrances for Perfume and House-
hold Chemistry (Pishchevaya Promyshlennost’, Mos-
cow, 1997) [in Russian].
Under these conditions, the condensation of 2-
pentylcyclopent-2-en-1-one with ethylene glycol also
proceeds with high selectivity and the yield of the
desired product reaches 71.5%.
5. O. G. Vyglazov, V. A. Chuiko, L. V. Izotova, et al.,
Russ. J. Appl. Chem. 74, 1888 (2001).
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Other Perfumery Materials (Khimiya, Moscow, 1994)
[in Russian].
The structure of the spiroacetals obtained was con-
firmed by IR, 1H and 13C NMR, and GC–MS data.
7. A. L. Maximov, A. I. Nekhaev, and D. N. Ramazanov,
Pet. Chem. 55, 1 (2015).
5-Pentylidene-1,4-dioxaspiro[4.4]nonane. Yield
8. D. N. Ramazanov, A. Dzhumbe, A. I. Nekhaev, et al.,
d420
nD20
Pet. Chem. 55, 140 (2015).
69.8%. Tb 102–104°C/0.26 kPa.
0.9685.
9. S. N. Khadzhiev, A. L. Maksimov, D. N. Ramazanov,
1.4654. IR, ν1, cm−1: 3040 (ν1 =CH), 2865 (ν1 CH2),
1630 (ν1 C=C), 1265, 1215, 1170, 850 (ν1 C–O–C)
and A. I. Nekhaev, RU Patent No. 2522764 (2014).
10. A. L. Maksimov, A. I. Nekhaev, D. N. Ramazanov,
1
[16, 17]. H NMR, δ, ppm: 0.92 (t, 3H, CH3, J =
et al., Pet. Chem. 51, 61 (2011).
8.1 Hz), 1.27–1.30 (m, 4H, 2CH2 alkyl), 1.35–1.94
(m, 6H, 3CH2 cycle), 4.0–4.05 (d, 4H, 2CH2, J = 7.2
Hz), 5.5 (d, 1H1=CH1, J = 6.3 Hz) [18].
11. Z. Jang, C. Lei, C. Zhao, et al., Chem. Select, No. 2,
9377 (2017).
12. Kh. M. Alimardanov, O. A. Sadygov, M. F. Abbasov,
and E. T. Suleimanova, Russ. J. Org. Chem. 47, 1153
(2011).
13. N. S. Abbaszade, M. F. Abbasov, and Kh. M. Alimar-
danov, in Proceedings of Republican Scientific-Practical
Conference Devoted to 100th Anniversary of Academy
Member S. D. Mekhtiev, vol. 1, p. 12 (2014).
14. O. A. Sadygov, N. S. Abbaszade, S. M. Abbasova, and
Kh. M. Alimardanov, Azerb. Khim. Zh., No. 1, 18
(2013).
5-Pentyl-1,4-dioxaspiro[4.4]non-5-ene.
Yield
71.5%. T 97–99/0.26 kPa. 20 0.9998. 20 1.4863. IR,
d4
nD
b
ν1, cm−1: 3045, 3020 (ν1 =CH), 2860 (ν1 =CH2), 1630
(ν1 C=C), 1470 (δ, CH3), 1260, 1210, 1170, 850 (ν1 C–
1
O–C). H NMR, δ, ppm: 0.91 (t, 3H, CH3, J =
8.1 Hz), 1.29–2.26 (m, 12H, 6CH2), 3.90 (d, 4H,
2OCH2, J = 7.1 Hz), 5.35 (d, 1H1=CH, J = 6.3 Hz).
15. G. I. Golodets, Teor. Eksp. Khim. 18, 37 (1982).
16. A. J. Gordon and R. A. Ford, The Chemist’s Compan-
The synthesized spiroacetals have a jasmine scent
and can be used as fragrances.
ion (Wiley–Interscience, New York,1972).
17. N. B. Colthupm, L. H. Daiy, and S. E. Wiberiey, Intro-
duction to Infrared and Raman Spectroscopy (Academic,
Boston, 1990).
In summary, it has been shown that zirconyl sul-
fate-modified samples of the natural aluminosilicate
perlite exhibit high activity in the condensation of the
unsaturated ketones 2-pentylidenecyclopentanone
and 2-pentylcyclopent-2-en-1-one with ethylene gly-
col to corresponding spiroacetals.
18. A. E. Derome, Modern NMR Techniques for Chemistry
Research (Pergamon, Oxford, 1987).
Translated by E. Boltukhina
PETROLEUM CHEMISTRY Vol. 59 No. 6 2019