2
410
GAZIZOV et al.
–
1
+
2
,8,14,20-Tetra-(2-N,N-diethylamino)ethylpenta-
IR spectrum, ν, cm : 1603 (arom.), 2723 (NH ), 3172
(OH). Found, %: С 63.38; Н 7.30; N 3.42; Cl 8.90.
3
,7 9,13 15,19
cyclo[19.3.1.1 .1 .1 ]octacosa-1(25),3,5,7(28),9,
1
1
,13-(27),15,17,19(26),21,23-dodecaene-4,6,10,12,16,
8,22,24-octol hydrochloride (II). A mixture of 0.58 g
С Н30ClNО . Calculated, %: С 63.71; Н 7.58; N 3.53;
Cl 8.97.
21 4
of 2-methylresorcinol, 0.95 g of acetal I, 5 ml of
ethanol, 5 ml of distilled water, and 2.1 ml of con-
centrated hydrochloric acid was heated for 0.5 h at 50°С
and then kept for 3 days at 20°С. The precipitate
formed was separated from the reaction mixture and
reprecipitated from chloroform into pentane, and the
light powder obtained was dried in a vacuum (5 h,
1
13
Н and С NMR spectra were registered on an
Avance 600 instrument with operating frequencies
6
00.13 and 150.90 MHz, respectively, relative to the
signals of residual protons of a deuterated solvent
D O, СD OD). The IR spectra were registered on a
(
2
3
–1
UR-20 spectrometer in the range of 400–3600 cm
from the paste in mineral oil or from thin layer.
0
.01 mm Hg) to constant weight. 0.74 g (58.2%) of
1
compound II was obtained, mp above 250°C. The Н
ACKNOWLEDGMENTS
NMR spectrum (СD OD), δ, ppm: 1.09–1.67 m (12Н,
3
СН ), 2.01–2.23 m (20Н, СН С , СН СН), 3.12–
3
3
arom
2
This work was financially supported by the Russian
Foundation for Basic Research (project no. 08-03-
3
.42 m (8Н, СН N), 4.41–4.62 m (4Н, СН), 6.71–7.10
2
–
1
m (4Н, СНarom). IR spectrum, ν, cm : 1600 (arom.),
0
0512).
3
1
100–3500 (ОН). Found, %: C 61.53; H, 8.68; Cl
2.98; N 5.01. C H C N O . Calculated, %: C 61.87;
5
6
88 l4
4
8
REFERENCES
H 8.16; Cl 13.04; N 5.15.
-(N,N-Diethylamino)-2,2-dimethyl-3,3-bis(2,4-
dihydroxy-3-methylphenyl)propane hydrochloride
IV). A mixture of 1.73 g of 2-methylresorcinol, 0.9 g
1
2
3
.
.
.
Burilov, A.R., Volodina, Yu.M., Gazizov, A.S., Knya-
zeva, I.R., Pudovik, M.A., Habicher, W., Baer, I., and
Konovalov, A.I., Chemicke Listy, 2004, vol. 98, no. 1,
p. 94.
Burilov, A.R., Gazizov, A.S., Volodina, Yu.M.,
Pudovik, M.A., Habicher, W., Baer, I., Gubaidullin, A.T.,
Litvinov, I.A., and Konovalov, A.I., Mendeleev
Commun., 2005, no. 4, p. 153.
1
(
of dimethylaminodimethylpropanal (III) [7], 3 ml of
concentrated hydrochloric acid, and 9 ml of distilled
water was heated for 2 h at 60°С. The solvent was then
removed and the residue was reprecipitated from
ethanol into diethyl ether. The precipitate formed was
dried in a vacuum (5 h, 0.01 mm Hg). 2.6 g (94.2 %)
Burilov, A.R., Gazizov, A.S., Volodina, Yu.M.,
Pudovik, M.A., Habicher, V.D., and Konovalov, A.I.,
Izv. Akad. Nauk, Ser. Khim., 2004, no. 11, p. 2543.
1
of compound IV was obtained, mp 120°С. Н NMR
spectrum (D O), δ, ppm (J, Hz): 1.03 s (6Н, СMe ),
2
2
4. Burilov, A.R., Gazizov, A.S., Kharitonova, N.I.,
Pudovik, M.A., and Konovalov, A.I., Zh. Obshch.
Khim., 2007, vol. 77, no. 3, p. 523.
5. Burilov, A.R., Gazizov, A.S., Pudovik, M.A., and
Konovalov, A.I., Zh. Obshch. Khim., 2007, vol. 77, no. 1,
p. 105.
6. Witzemann, J., Evans, W.L., Hass, H, and Schroeder, E.F.,
Org. Synth., 1943, vol. 2, p. 137.
7. Mannich, C., Lesser, B., and Silten, F., Chem. Ber.,
2
.03 s (6Н, ССН ), 2.70 s (6Н, NMe ), 2.92 s (2Н,
3 2
ССН N), 5.04 s (1Н, СН), 6.47 d (2Н, ortho-СН
,
С
CH
8
2
arom
3
3
13
JНН 8.6), 7.18 d (2Н, meta-СНarom, J 8.6).
НН
1
1
NMR spectrum (D O) δ, ppm (J, Hz): 9.10 (С , J
2
1
0
1
9
1
27.8), 23.78 (С , J 127.5), 38.90 (С ), 39.24 (С ,
CH
12
1
1
11 1
JCH 126.6), 46.99 (С , J 144.2), 69.67 (С , J
CH
CH
6
1
2
1
44.5), 108.39 (С , J 159.7), 112.89 (С ), 121.89
CH
4
5
1
7
3
(
С ), 128.15 (С , J 159.7), 152.95 (С ), 153.16 (С ).
CH
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 78 No. 12 2008