BEZBORODOV, KOVGANKO
1298
J = 7 Hz), 0.93 t (3H, C5'H3, C8''H3, J = 7 Hz), 1.30–
1.68 m (12H, CH2, alkyl), 1.82 quint (2H, C2'H2, J =
7 Hz), 3.04 d.d (1H, C2"H2, J1 = 9, J2 = 18 Hz),
3.16 d.d (1H, C2"H2, J1 = 2.4, J2 = 18 Hz), 3.23 d (1H,
3-OH, J = 3 Hz), 4.04 t (2H, C1'H2, J = 7 Hz), 4.16–
4.26 m (1H, 3"-H), 6.96 d (2H, Harom, J = 9 Hz), 7.31 d
(2H, Harom, J = 9 Hz), 8.02 d (2H, Harom, J = 9 Hz),
8.12 d (2H, Harom, J = 9 Hz).
(C=O, ester); 1680 (C=O, ketone); 1600, 1580, 1510
1
(C=Carom). H NMR spectrum, δ, ppm: 0.87 t (3H,
C9'H3, C8''H3, J = 7 Hz), 0.89 t (3H, C9'H3, C8''H3, J =
7 Hz), 1.16–1.69 m (20H, CH2, alkyl), 1.81 quintet
(2H, C2'H2, J = 7 Hz), 3.03 d.d (1H, C2"H2, J1 = 9, J2 =
18 Hz), 3.17 d.d (1H, C2"H2, J1 = 2.5, J2 = 18 Hz),
3.25 br.s (1H, OH), 4.03 t (2H, C1'H2, J = 7 Hz), 4.18–
4.26 m (1H, 3"-H), 6.96 d (2H, Harom, J = 9 Hz), 7.31 d
(2H, Harom, J = 9 Hz), 8.02 d (2H, Harom, J = 9 Hz),
8.12 d (2H, Harom, J = 9 Hz).
4-(3-Hydroxyoctanoyl)phenyl 4-hexyloxyben-
zoate (Vd). Yield 84%. IR spectrum, ν, cm–1: 3200–
3650 (OH); 3035, 3015 (C–Harom); 2960, 2935, 2875,
2860 (C–Halkyl); 1735 (C=O, ester); 1680 (C=O,
4-(3-Hydroxyoctanoyl)phenyl 4-dodecyloxyben-
zoate (Vh). Yield 72%. IR spectrum, ν, cm–1: 3240–
3630 (OH); 3015 (C–Harom); 2955, 2930, 2855
(C–Haliph); 1735 (C=O, ester); 1675 (C=O, ketone);
1
ketone); 1605, 1585, 1515 (C=Carom). H NMR spec-
trum, δ, ppm: 0.85–0.94 m (6H, C6'H3, C8''H3), 1.20–
1.67 m (14H, CH2, alkyl), 1.81 quintet (2H, C2'H2, J =
7 Hz), 3.03 d.d (1H, C2"H2, J1 = 9, J2 = 18 Hz),
3.16 d.d (1H, C2"H2, J1 = 2.4, J2 = 18 Hz), 3.24 d (1H,
OH, J = 3.2 Hz), 4.03 t (2H, C1'H2, J = 7 Hz), 4.17–
4.26 m (1H, 3"-H), 6.96 d (2H, Harom, J = 9 Hz), 7.31 d
(2H, Harom, J = 9 Hz), 8.02 d (2H, Harom, J = 9 Hz),
8.12 d (2H, Harom, J = 9 Hz).
1
1600, 1580, 1505 (C=Carom). H NMR spectrum, δ,
ppm: 0.88 t (3H, C12'H3, C8''H3, J = 6.8 Hz), 0.91 t (3H,
C12'H3, C8''H3, J = 6.8 Hz), 1.18–1.68 m (26H, CH2,
alkyl), 1.82 quintet (2H, C2'H2, J = 6.8 Hz), 3.04 d.d
(1H, C2"H2, J1 = 9, J2 = 17.6 Hz), 3.18 d.d (1H, C2"H2,
J1 = 2.4, J2 = 17.6 Hz), 3.23 d (1H, OH, J = 2.9 Hz),
4.06 t (2H, C1'H2, J = 6.8 Hz), 4.17–4.27 m (1H, 3"-H),
6.98 d (2H, Harom, J = 8.8 Hz), 7.32 d (2H, Harom, J =
8.8 Hz), 8.04 d (2H, Harom, J = 8.8 Hz), 8.13 d (2H,
Harom, J = 8.8 Hz).
4-(3-Hydroxyoctanoyl)phenyl 4-heptyloxyben-
zoate (Ve). Yield 65%. IR spectrum, ν, cm–1: 3250–
3630 (OH); 3030, 3010 (C–Harom); 2955, 2930, 2870,
2855 (C–Haliph); 1735 (C=O, ester); 1675 (C=O,
4-(3-Hydroxyoctanoyl)phenyl 4-hexadecyloxy-
benzoate (Vi). Yield 92%. IR spectrum, ν, cm–1:
3200–3630 (OH); 3025 (C–Harom); 2925, 2850
(C–Haliph); 1730 (C=O, ester); 1675 (C=O, ketone);
1
ketone); 1600, 1580, 1505 (C=Carom). H NMR spec-
trum, δ, ppm: 0.84–0.95 m (6H, C7'H3, C8''H3), 1.20–
1.67 m (16H, CH2, alkyl), 1.81 quint (2H, C2'H2, J =
7 Hz), 3.03 d.d (1H, C2"H2, J1 = 9, J2 = 17.6 Hz),
3.16 d.d (1H, C2"H2, J1 = 2.4, J2 = 17.6 Hz), 3.22 d
(1H, OH, J = 3.2 Hz), 4.03 t (2H, C1'H2, J = 7 Hz),
4.17–4.26 m (1H, 3"-H), 6.96 d (2H, Harom, J = 9 Hz),
7.31 d (2H, Harom, J = 9 Hz), 8.02 d (2H, Harom, J =
9 Hz), 8.12 d (2H, Harom, J = 9 Hz).
1
1600, 1580, 1505 (C=Carom). H NMR spectrum, δ,
ppm: 0.86 t (3H, C16'H3, C8''H3, J = 6.8 Hz), 0.89 t (3H,
C16'H3, C8''H3, J = 6.8 Hz), 1.17–1.67 m (34H, CH2,
alkyl), 1.81 quintet (2H, C2'H2, J = 6.8 Hz), 3.03 d.d
(1H, C2"H2, J1 = 8.8, J2 = 18 Hz), 3.17 d.d (1H, C2"H2,
J1 = 2.4, J2 = 18 Hz), 3.22 d (1H, OH, J = 2.4 Hz),
4.03 t (2H, C1'H2, J = 6.8 Hz), 4.17–4.27 m (1H, 3"-H),
6.96 d (2H, Harom, J = 8.8 Hz), 7.31 d (2H, Harom, J =
8.8 Hz), 8.02 d (2H, Harom, J = 8.8 Hz), 8.12 d (2H,
Harom, J = 8.8 Hz).
4-(3-Hydroxyoctanoyl)phenyl 4-octyloxyben-
zoate (Vf). Yield 86%. IR spectrum, ν, cm–1: 3260–
3650 (OH); 3035, 3015 (C–Harom); 2960, 2935, 2870,
2860 (C–Haliph); 1735 (C=O, ester); 1680 (C=O,
1
ketone); 1605, 1580, 1515 (C=Carom). H NMR spec-
4-(3-Hydroxyoctanoyl)phenyl 4-hexylbenzoate
(Vj). Yield 67.4%, mp 104–104.5°C (from 2-pro-
panol). IR spectrum, ν, cm–1: 3200–3630 (OH); 3010
(C–Harom); 2955, 2930, 2855 (C–Haliph); 1735 (C=O,
ester); 1670 (C=O, ketone); 1600, 1500 (C=Carom).
1H NMR spectrum, δ, ppm: 0.88 t (3H, C6'H3, C8''H3,
J = 6.8 Hz), 0.89 t (3H, C6'H3, C8''H3, J = 6.8 Hz),
1.22–1.69 m (16H, CH2 alkyl), 2.69 t (2H, C1'H2, J =
8 Hz), 3.04 d.d (1H, C2"H2, J1 = 9, J2 = 17.6 Hz),
3.17 d.d (1H, C2"H2, J1 = 2.4, J2 = 17.6 Hz), 3.22 d
(1H, OH, J = 3.2 Hz), 4.17–4.26 m (1H, 3"-H), 7.31 d
(2H, Harom, J = 8.8 Hz), 7.32 d (2H, Harom, J = 8.4 Hz),
trum, δ, ppm: 0.85–0.95 m (6H, C8'H3, C8''H3), 1.20–
1.68 m (18H, CH2, alkyl), 1.81 quint (2H, C2'H2, J =
7 Hz), 3.03 d.d (1H, C2"H2, J1 = 9, J2 = 17.6 Hz),
3.16 d.d (1H, C2"H2, J1 = 2.4, J2 = 17.6 Hz), 3.23 d
(1H, OH, J = 3.2 Hz), 4.03 t (2H, C1'H2, J = 7 Hz),
4.16–4.26 m (1H, 3"-H), 6.96 d (2H, Harom, J = 9 Hz),
7.31 d (2H, Harom, J = 9 Hz), 8.02 d (2H, Harom, J =
9 Hz), 8.12 d (2H, Harom, J = 9 Hz).
4-(3-Hydroxyoctanoyl)phenyl 4-nonyloxyben-
zoate (Vg). Yield 70.4%. IR spectrum, ν, cm–1: 3035,
3015 (C–Harom); 2960, 2940, 2865 (C–Halkyl); 1735
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 40 No. 9 2004