KHUSNUTDINOV et al.
1550
1-(2,4-Dimethylphenyl)adamantane (26). Yield
The study was carried out under the financial
support of the Russian Foundation for Basic Research
(grant no. 14-03-97029r_povolzh’e-а) and of a
Program of the President of Russian Federation for
support of young scientists and postgraduate students
carrying out promising scientific research and
development in the priority fields of modernizing the
Russian economy (SP-4810.2013.4) for 2013–2015.
19%, mp 144–145°С (methanol) (144–146°С [14]).
13С NMR spectrum, δ, ppm: 21.46 (Me), 21.71 (Me),
29.17 (С3,5,7), 35.68 (С1), 37.03 (С4,6,9), 43.38 (С2,8,10),
124.72 (С16), 125.29 (С15), 132.19 (С13), 135.95 (С12),
150.88 (С11). Found, %: С 89.57; Н 10.43. С18Н24.
Calculated, %: С 89.94; Н 10.06.
4-(1-Adamantyl)-2-methylphenol (28). Yield 99%,
mp 137–138°С (ethanol). 13С NMR spectrum, δ, ppm:
16.31 (Me), 29.19 (С3,5,7), 36.72 (С1), 36.99 (С4,6,9), 42.82
(С2,8,10), 114.45 (С15), 123.51 (С13), 125.61 (С16), 127.22
(С12), 143.52 (С11), 151.49 (С14). Found, %: С 83.88;
Н 9.05. С17Н22О. Calculated, %: С 84.25; Н 9.15.
REFERENCES
1. Roginskii, V.A., Fenol’nye antioksidanty. Reaktsion-
naya sposobnost’ i effektivnost’ (Phenolic Antioxidants.
Reactivity and Efficiency), Moscow: Nauka, 1998.
2. Sokolenko, V.A., Svirskaya, N.M., Velikov, A.A., and
6-(1-Adamantyl)-3-methylphenol (30). Yield
84%, mp 116–117°С (ethanol) (116–117.5°С [15]).
13С NMR spectrum, δ, ppm: 20.24 (Me), 29.07 (С3,5,7),
35.98 (С1), 36.73 (С4,6,9), 42.41 (С2,8,10), 117.89 (С13),
120.99 (С15), 126.22 (С16), 132.67 (С11), 138.70 (С14),
146.17 (С12). Found, %: С 83.98; Н 9.07. С17Н22О.
Calculated, %: С 84.25; Н 9.15.
Sizova, N.V., Kinet. Catal., 2002, vol. 43, p. 185.
3. Danilenko, G.I., Shablovskaya, E.A., Antonova, L.A.,
Guzhova, S.V., Lobanova, I.A., Dyachenko, A.P., and
Panasyuk, A.I., Pharm. Chem. J., 1998, vol. 32, p. 83.
4. Carpentier, B., Bernadon, J.-M., Eustache, J., Millois, C.,
Martin, B., Michel, S., and Shroot, B., J. Med. Chem.,
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5. Gogotov, A.F., Do, Ch.T., Sоkolenko, W.A., Svirs-
kaya, N.M., Dam T.Th.H., Rudenko, D.S., Peterson, I.V.,
Rubaylo, A.I., and Stankevich, V.K., Neftepererab.
Neftekh., 2013, p. 18.
2-(1-Adamantyl)-4-methylphenol (32). Yield
90%, mp 128–129°С (ethanol) (127–129°С [15]). 13С
NMR spectrum, δ, ppm: 20.60 (Me), 29.12 (С3,5,7),
35.59 (С1), 37.14 (С4,6,9), 40.75 (С2,8,10), 117.67 (С13),
126.86 (С16), 128.99 (С14), 130.10 (С15), 136.70 (С11),
152.23 (С12). Found, %: С 83.95; Н 9.09. С17Н22О.
Calculated, %: С 84.25; Н 9.15.
6. Tsypin, V.G. and Golod, E.L., Russ. J. Org. Chem.,
1998, vol. 34, p. 1059.
7. Moiseev, I.K., Bagrii, E.I., Klimochkin, Yu.N.,
Dolgopolova, T.N., Zemtsova, M.N., and Trakhten-
berg, P.L., Russ. Chem. Bull., 1985, vol. 34, p. 1983.
2-(1-Adamantyl)-4,5-dimethylphenol (34). Yield
36%, mp 144–145°С. 13С NMR spectrum, δ, ppm:
18.96 (Me), 19.24 (Me), 29.37 (С3,5,7), 34.68 (С1),
36.53 (С4,6,9), 42.41 (С2,8,10), 115.13 (С13), 125.87
(С16), 128.62 (С15), 132.37 (С11), 135.19 (С14), 143.29
(С12). Found, %: С 83.95; Н 9.30. С17Н22О.
Calculated, %: С 84.32; Н 9.44.
8. Kovalev, V.V. and Shokova, E.A., Zh. Org. Khim.,
1985, vol. 21, p. 2085.
9. Wang, N., Wang, R., Shi, X., and Zou, G., Beilstein
J. Org. Chem., 2012, vol. 8, p. 227.
10. Voronkov, A.V., Aliev, A.A., Kutrakov, A.V., and Voron-
kov, V.V., Russ. J. Org. Chem., 1999, vol. 35, p. 305.
11. Ghorai, S.K., Jin, M., Hatakeyama, T., and Nakamu-
ra, M., Org. Lett., 2012, vol. 14, p. 10.
12. Nishimoto, Y., Onishi, Y., Yasuda, M., and Bara, A.,
2-(1-Adamantyl)-3,5-dimethylphenol (36). Yield
13
66%, mp 135–136°С (ethanol). С NMR spectrum, δ,
ppm: 21.29 (Me), 21.35 (Me), 29.17 (С3,5,7), 35.68
(С1), 36.53 (С4,6,9), 43.41 (С2,8,10), 114.63 (С13), 124.27
(С15), 134.38 (С11), 135.43 (С16), 135.69 (С14), 152.44
(С12). Found, %: С 83.85; Н 9.04. С17Н22О. Cal-
culated, %: С 84.32; Н 9.44.
Angew. Chem., Int. Еd., 2009, vol. 48, p. 9131.
13. Ambartsumyan, A.A., Vasil’eva, T.T., Chakhovskaya, O.V.,
Mysova, N.E., and Kochetkov, K.A., Russ. J. Org. Chem.,
2014, vol. 50, p. 752.
14. Moiseev, I.K. and Doroshenko, R.I., Zh. Org. Khim.,
1-(2,3,5,6-Tetramethylbenzene)adamantane (38).
Yield 31%, mp 70–72°С (methanol). 13С NMR spectrum,
δ, ppm: 16.53 (2 Me), 20.35 (2 Me), 28.57 (С3,5,7), 34.38
(С1), 36.83 (С4,6,9), 43.71 (С2,8,10), 129.79 (С12,16), 128.17
(С14), 134.18 (С13,15), 153.74 (С11). Found, %: С 89.05;
Н 10.95. С20Н28. Calculated, %: С 89.49; Н 10.51.
1982, vol. 18, p. 1233.
15. Aigami, K., Inamoto, Y., Takaishi, N., and Hattori, K.,
J. Med. Chem., 1975, vol. 18, p. 713.
16. Chailais, S., Cornelis, A., Gerstmans, A., Kolodziejski, W.,
Laszlo, P., Mathy, A., and Metra, P., Helv. Chim. Acta,
1985, vol. 68, p. 1196.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 11 2015