ONE-POT OZONOLYTIC SYNTHESIS
939
Methyl 10-hydroxydecanoate (3). Rf 0.30 (petroleum
ether–methyl tert-butyl ether, 2 : 1). The 1Н and 13С NMR
spectra are identical to those reported in [35].
(including preparative procedures) for the synthesis
of a series of acyclic α,ω-bifunctional compounds that
are widely used in medicine, perfumery, cosmetology,
engineering, and chemical industry and are valuable
block synthons for targeted organic synthesis, including
synthesis of low-molecular-mass insect pheromones.
Ozonolysis of 10-undecen-1-ol (2) in isopropanol.
The chromatographic separation (SiO2, petroleum ether–
methyl tert-butyl ether, 2 : 1) of the residue (1.03 g)
obtained using method а yielded 0.54 g (47%) of hydroxy
ester 9 and 0.34 g (40%) of hydroxy nitrile 10. By
method b, 1.08 g (94%) of hydroxy ester 9 was obtained.
REFERENCES
1. Biologicheskii entsiklopedicheskii slovar’ (Biological
Encyclopedic Dictionary), Gilyarov, M.S., Ed., Moscow:
Sov. Entsiklopediya, 1986.
Isopropyl 10-hydroxydecanoate (9). Rf 0.36
(petroleum ether–methyl tert-butyl ether, 2 : 1). IR
spectrum, ν, cm–1: 1741 and 1737 (ester С=О), 1174–1234
(С–О–С), 3300 (ОН). 1Н NMR spectrum, δ, ppm: 1.22 d
(6Н, 2СН3), 1.22–1.61 m (14Н, 7СН2), 2.25–2.40 m (2Н,
СН2СОО), 3.40–3.58 m (2Н, СН2ОН), 4.82–5.08 m
[1Н, СООСН(СН3)2], 5.41 br.s (1Н, ОН). 13С NMR
spectrum, δ, ppm: 21.80 [COOCH(CH3)2], 22.34,
23.81, 24.59, 25.66, 26.73, 29.64 (С-3–С-8), 32.51
(CH2CH2OН), 33.68 (CH2COO), 62.34 (CH2OН), 68.47
[COOCH(CH3)2], 173.56 (СООPri).
2. Maznev, N.I., Lekarstvennye rasteniya (Medicinal Herbs),
Moscow: Dom XXI Vek, 2006.
3. Ishmuratov, G.Yu., Yakovleva, M.P., and Tolstikov, G.A.,
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10-Hydroxydecanonitrile (10). Rf 0.25 (petroleum
ether–methyl tert-butyl ether, 2 : 1). IR spectrum (KBr), ν,
cm–1: 2220 (СN), 3300 (OН). 1Н NMR spectrum, δ, ppm:
1.22–1.84 m (14Н, СН2-3–СН2-9), 2.43 m (2Н, СН2-2),
3.41 m (2Н, СН2-10), 5.50 br.s (1Н, ОН). 13С NMR
spectrum, δ, ppm: 18.02 (С-2), 25.26 (С-3), 26.25 (С-8),
28.41 (С-7), 29.02 (С-5), 29.42 (С-6), 29.62 (С-4), 34.40
(С-9), 62.86 (С-10), 119.12 (СN).
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Synthesis, 1974, p. 718.
Ozonolysis of 10-undecen-1-ol (2) in an acetic
acid–methylene chloride mixture. The chromatographic
separation (SiO2, petroleum ether–methyl tert-butyl ether,
2 : 1) of the residue (1.20 g) obtained using method а
yielded 0.23 g (24%) of hydroxy acid 11 and 0.83 g (72%)
of 10-acetoxydecanoic acid (12). By method b, 0.20 g
(21%) of hydroxy acid 11 and 0.87 g (76%) of acetate
12 were obtained.
11. Ishmuratov, G.Yu., Legostaeva, Yu.V., Nasibullina, G.V.,
et al., Chem. Natural Compd., 2014, vol. 50, no. 4,
pp. 594–597.
12. Ishmuratov, G.Yu., Shayakhmetova, A.Kh., Yakovle-
va, M.P., et al., Russ. J. Org. Chem., 2007, vol. 43, no. 8,
pp. 1114–1119.
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10-Hydroxydecanoic acid (11). Rf 0.10 (petroleum
ether–methyl tert-butyl ether, 3 : 1). The 1Н and 13С NMR
spectra are identical to those described in [37].
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10-Acetoxydecanoic acid (12). Rf 0.20 (petroleum
ether–methyl tert-butyl ether, 3 : 1). The 1Н and 13С NMR
spectra are identical to those described in [34].
CONCLUSIONS
21. Gryglewicz, S., Stankiewicz, M., Oko, F.A., and
Asystematic study of transformations of peroxy prod-
ucts formed by ozonolysis of methyl 10-undecenoate and
10-undecen-1-ol allowed the development of procedures
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RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 88 No. 6 2015