906
DEKHTYAR’ et al.
(C1, CH), 126.48 128.28 (C2 C6 , CH, Ar), 142.42
(C1 , C, Ar). Found, %: C 78.10; H 11.00. C19H32O2.
Calculated, %: C 78.03; H 10.94.
2-(1,4-Dimethyl-1-phenyldecyloxy)ethan-1-ol
1
(IIIe), bp 180 185 C (5 mm Hg). H NMR spectrum,
, ppm: 0.85 t (3H, H10, CH3, J 7.0 Hz), 0.90 d (3H,
H11, CHCH3, J 5.7 Hz), 1.13 d (3H, H3 , CH3, J
5.8 Hz), 1.15 1.95 m (15H, H2 H9, CH2, CH),
2.11 br.s (1H, OH), 3.45 t (2H, H2 , CH2, J 5.2 Hz),
3.50 3.60 m (1H, H1 , CHO,), 7.20 7.40 m (5H, H2
H6 , CH, Ar). 13C NMR spectrum, C, ppm: 14.06
2-(3-Ethyl-1-phenylnonyloxy)ethan-1-ol (IVc),
bp 120 125 C (1 mm Hg). 1HNMR spectrum, , ppm:
0.84 t (3H, H11, CHCH3, J 5.1 Hz), 0.86 t (3H, H9,
CH3, J 6.0 Hz), 1.15 1.45 m (10H, H4 H8, CH2),
1.45 1.55 m (2H, H10, CH2), 1.65 1.75 m (2H, H2,
CH2), 1.75 1.95 m (1H, H3, CH), 2.17 br.s (1H, OH),
3.43 t (2H, H1 , CH2O, J 7.7 Hz), 3.70 t (2H, H2 ,
CH2OH, J 7.7 Hz), 4.32 t (1H, H1, CH, J 6.8 Hz),
7.20 7.40 m (5H, H2 H6 , CH, Ar). 13C NMR spec-
(C10, CH3) 17.56 (C3 , CH3), 19.55 (C11, CHCH3),
22.64 (C9, CH2), 29.57 (C7, CH2), 29.71 (C6, CH2),
31.86 (C8, CH2), 32.75 (C4, CH), 35.91 (C5, CH2),
36.04 (C2, CH2), 36.80 (C3, CH2), 65.65 (C2 ,
trum, C, ppm: 10.45 (C11, CH3), 13.99 (C9, CH3),
22.55 (C8, CH2), 26.03 (C5, CH2), 26.84 (C10, CH2),
CH2OH), 74.27 (C1 , CHO), 81.71 (C1, CH), 126.60
128.49 (C2 C6 , CH, Ar), 143.98 (C1 , C, Ar). Found,
%: C 78.40; H 12.01. C20H34O2. Calculated, %: C
78.38; H 11.18.
29.54 (C6, CH2), 31.77 (C7, CH2), 35.06 (C3, CH),
35.47 (C4, CH2), 42.19 (C2, CH2), 61.79 (C2 ,
CH2OH), 69.75 (C1 , CH2O), 80.90 80.98 (C1, CH),
126.48 128.28 (C2 C6 , CH, Ar), 142.34 (C1 , C, Ar).
Found, %: C 78.10; H 11.00. C19H32O2. Calculated,
%: C 78.03; H 10.94.
2-(1,4-Dimethyl-1-phenyldecyloxy)ethan-1-ol
1
(IVe), bp 180 185 C (5 mm Hg). H NMR spectrum,
, ppm: 0.85 t (3H, H11, CH3, J 7.1 Hz), 0.95 t (3H,
H9, CH3, J 6.6 Hz), 1.13 d (3H, H3 , CH3, J 5.8 Hz),
1.15 1.95 m (15H, H2 H8, H10, CH2, CH), 2.11 br.s
(1H, OH), 3.49 t (2H, H2 , CH2, J 6.6 Hz), 3.50
3.60 m (1H, H1 , CHO,), 7.20 7.40 m (5H, H2 H6 ,
CH, Ar). 13C NMR spectrum, C, ppm: 10.53 (C11,
CH3), 14.06 (C9, CH3), 17.64 (C3 , CH3), 22.64 (C8,
2-(1-Isopropyl-4-methyldecyloxy)ethan-1-ol
1
(IIId), bp 145 150 C (40 mm Hg). H NMR spec-
trum, , ppm: 0.89 t (3H, H10, CH3, J 6.6 Hz), 0.9 d
(3H, H11, CHCH3, J 5.2 Hz), 0.91 d (6H, H2 , H3 ,
CH3, J 6.7 Hz), 1.05 1.55 m (15H, H2 H9, CH2, CH),
1.80 1.92 m (1H, H1 , CH), 2.25 br.s (1H, OH), 2.97
3.07 m (1H, H1, CH), 3.55 t (2H, H1 , CH2O, J
7.0 Hz), 3.72 t (2H, H2 , CH2OH, J 7.0 Hz). 13C NMR
CH2), 26.05, 26.37 (C10, CH2) 26.11 (C5, CH2), 29.66
(C6, CH2), 31.86 (C7, CH2), 35.21 (C3, CH), 35.91
(C4, CH2), 42.71, 42.77 (C2, CH2), 65.75 (C2 , CH2,
OH), 74.45 (C1 , CHO), 79.49 (C1, CH), 126.60
128.49 (C2 C6 , CH, Ar), 143.90 (C1 , C, Ar). Found,
%: C 78.40; H 12.01. C20H34O2. Calculated, %: C
78.38; H 11.18.
spectrum, C, ppm: 14.06 (C10, CH3), 18.03 (C2 , CH3),
18.23 (C3 , CH3), 19.60, 19.71 (C11, CHCH3), 22.65
(C9, CH2), 27.01 (C6, CH2), 27.72 (C2, CH2), 29.63
(C7, CH2), 30.65 (C4, CH), 31.90 (C8, CH2), 32.76,
32.86 (C3, CH2), 32.90, 33.01 (C1 , CH), 36.90 (C5,
CH2), 62.25 (C2 , CH2OH), 70.70 (C1 , CH2O), 85.37,
85.47 (C1, CH). Found, %: C 73.36; H 13.13.
C16H34O2. Calculated, %: C 74.36; H 13.26.
ACKNOWLEDGMENTS
The work was financially supported by the Russian
Foundation for Basic Research, State Support for
Integration of Higher Education and Basic Science
Program (project no. 425).
2-(3-Ethyl-1-isopropylnonyloxy)ethan-1-ol
(IVd), bp 145 150 C (40 mm Hg). 1H NMR spectrum,
, ppm: 0.87 t (3H, H11, CHCH3, J 6.7 Hz), 0.91 d
(6H, H2 , H3 , CH3, J 6.7 Hz), 0.92 t (3H, H9, CH3, J
6.9 Hz), 1.05 1.55 m (15H, H2 H8, H10, CH2, CH),
1.80 1.92 m (1H, H1 , CH), 2.25 br.s (1H, OH), 3.13
3.21 m (1H, H1, CH), 3.55 t (2H, H1 , CH2O, J
7.0 Hz), 3.72 t (2H, H2 , CH2OH, J 7.0 Hz). 13C NMR
spectrum, C, ppm: 10.30, 10.78 (C11, CHCH3), 14.06
(C9, CH3), 17.66, 17.83 (C3 , CH3), 18.13, 18.20 (C2 ,
REFERENCES
1. Comprehensive Organometallic Chemistry, Wilkin-
son, G., Ed., Oxford: Pergamon, 1982, vol. 1, p. 580.
2. Dzhemilev, U.M., Ibragimov, A.G., and Zolota-
rev, A.P., Izv. Akad. Nauk SSSR, Ser. Khim., 1989,
no. 1, p. 207.
CH3), 23.02 (C8, CH2), 26.23 (C5, CH2), 27.01 (C10,
CH2), 29.63 (C6, CH2), 30.61, 30.65 (C3, CH), 31.90
(C7, CH2), 33.72, 34.30 (C4, CH2), 35.59 (C1 , CH),
3. Dzhamilev, U.M., Ibragimov, A.G., Zolotarev, A.P.,
and Tolstikov, G.A., Izv. Akad. Nauk SSSR, Ser. Khim.,
1990, no. 12, p. 2831.
37.08 (C2, CH2), 62.25 (C2 , CH2OH), 70.47 (C2 ,
CH2O), 82.80 (C1, CH2). Found, %: C 73.36; H 13.13.
C16H34O2. Calculated, %: C 74.36; H 13.26.
4. Vostrikova, O.S., Dekhtyar’, E.F., Zlotskii, S.S., and
Dokichev, V.A., Izv. Ross. Akad. Nauk, Ser. Khim.,
2002, no. 5, p. 828.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 74 No. 6 2004