134
KERIMOV
4-(2-Chloroethoxymethyl)-2-cis-(1,2-epoxycyclo-
IR spectrum of dioxolane XLI contains no bands at
1
hexyl)-1,3-dioxolane (XXII). To a stirred mixture of
24.7 g of compound XIV and 50 ml of chloroform
(18 20 C) we added over the course of 30 min, 18.6 g
of 55% peracetic acid. Stirring was continued for an
additional 1.5 2 h, after which the reaction mixture
was treated with 5% aqueous sodium carbonate,
washed with water, and dried with MgSO4. The sol-
vent was removed, and the residue was distilled in a
800 and 920 cm and contains a broad band at 3450
1
3500 cm , characteristic of associated OH group.
ACKNOWLEDGMENTS
The author is deeply grateful to M.G. Babaev for
help in determining reaction rates and designing the
paper.
1
vacuum to isolate compound XXII. H NMR spec-
REFERENCES
trum, , ppm: 1.25 2.25 m (7H, carboring CH2CH2
1. Babaev, M.G., Kerimov, A.Kh., and Khalilov, Kh.D.,
Abstracts of Papers, 2 Mezhdunarodnaya nauchnaya
konferentsiya Tonkii organicheskii sintez i kataliz
(2nd Int. Scientific Conf. Fine Organic Synthesis and
Catalysis, Baku, 2002, pp. 102 103.
O
CHCH2), 2.95 d (2H, HC CH ), 3.25 4.30 m (7H,
CH2O, CHO, ClCH2CH2O), 4.55 d (1H, trans-OCHO,
J 8 Hz), 5.70 d (1H, cis-OCHO, J 8 Hz).
2. Kerimov, A.Kh., Babaev, M.G., and Mishiev, D.E.,
Zh. Org. Khim., 1985, vol. 21, no. 3, p. 645.
3. Kerimov, A.Kh., Babaev, M.G., and Mishiev, D.E.,
Zh. Org. Khim., 1987, vol. 23, no. 6, p. 1194.
4. US Patent 2113454, Chem. Abstr., 1972, vol. 77,
no. 25, N 164665.
5. Lebedev, N.N., Khimiya i tekhnologiya osnovnogo
organicheskogo i neftekhimicheskogo sinteza (Che-
mistry and Technology of the Ground Organic and
Petrochemical Synthesis), Moscow: Khimiya, 1975,
pp. 671 673.
6. Taganliev, A., Berdieva, E., Rol’nik, L.Z., Zlot-
skii, S.S., Rakhmankulov, D.L., and Samirkha-
nov, Sh.M., USSR Inventor’s Certificate no. 1553532,
Byull. Izobret., 1990, no. 12.
7. Trofimov, B.A., Atavin, A.S., and Gavrilova, G.M.,
USSR Inventor’s Certificate no. 281461, Byull.
Izobret., 1973, no. 25.
8. Bohm, R., Wiss. Z. Univ., 1980, vol. 29, no. 2, p. 97.
9. Ol’shanova, K.M., Potapova, M.A., and Morozo-
va, N.M., Praktikum po khromatograficheskomu
analizu (Manual on Chromatographic Analysis),
Moscow: Vysshaya Shkola, 1970, pp. 63 66.
10. Babaev, M.G., Kerimov, A.Kh., Mishiev, D.E., Ragi-
mov, A.V., and Shteinberg, B.Ya., Available from
VINITI, 1985, Moscow, no. 6895-B-85.
Compounds XXIII XXIX were synthesized in a
similar way.
4-(2-Chloroethoxymethyl)-2-(1,2-dibromocyclo-
hexyl)-1,3-dioxolane (XXX). Bromine, 33.6. g, was
added dropwise at 10 to 5 C to a stirred mixture of
49.3 g of compound XIV and 110 ml of carbon tetra-
chloride. The reaction mixture was stirred for an
additional 1.5 2 h at that temperature and washed
with 5% aqueous sodium hydroxide and water. The
aqueous layer was treated with carbon tetrachloride,
the extract was combined with the organic layer and
dried with MgSO4. The solvent was removed, and the
residue was distilled in a vacuum to isolate compound
1
XXX. IR spectrum, , cm : 660, 680 (C Br), 690,
820 (C Cl), 1020, 1225 (O C O). 1H NMR spectrum,
, ppm: 1.30 1.60 m (7H, carboring CH2CH2CHCH2),
3.25 4.40 m (7H, CH2O, CHO, ClCH2CH2O), 4.68 d
(3H, 3HCBr).
Compounds XXXI XXXVII were synthesized in a
similar way.
2-(1,8,9,10,11,11-Hexachlorotricyclo[6.2.1.02,7]-
undec-9-en-5-yl)-4-(2-chloroethoxymethyl)-1,3-di-
oxolane (XXXIX). A mixture of 24.7 g of compound
XIV and 54.6 g of HCCPD was stirred for 12 h at
140 150 C. Excess HCCPD was removed by distilla-
tion, and the residue was distilled in a vacuum to
obtain compound XXXIX.
11. Leidler, K., Kinetika organicheskikh reaktsii (Kinetics
of Organic Reactions), Moscow: Mir, 1966, pp. 341
345.
12. Sykes, P., A Guidebook to Mechanism in Organic
Chemistry, 2nd ed., London: Longmans, 1966. Trans-
lated under the title Mekhanizmy reaktsii v organi-
cheskoi khimii, Moscow: Khimiya, 1991, pp. 31 33.
13. Luknitskii, F.I., Chem. Rev., 1975, vol. 75, no. 3,
p. 259.
14. Laboratornye raboty po organicheskoi khimii (Lab-
oratory Works in Organic Chemistry), Ginzburg, O.F.
and Petrov, A.M., Moscow: Vysshaya Shkola, 1982,
pp. 240 254.
Compounds XXXVIII and XL were obtained in a
similar way (see table).
2-[2(1)-Chlorocyclohexyl-1(2)-hydroxy]-4-(2-
chloroethoxymethyl)-1,3-dioxolane (XLI). Hydro-
gen chloride was passed through a mixture of 39.4 g
of compound XXII and 50 ml of ether at 10 to 5 C
(the weight gain was determined by weighing). The
ether was removed by distillation, and the residue was
istilled in a vacuum to isolate compound XLI. The
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 73 No. 1 2003