SYNTHESIS, PHYSICOCHEMICAL PROPERTIES
689
2
0
43 (30). Found, %: C 76.14; H 11.16. Calculated for
C H O , %: C 76.14; H 11.18.
1
40–146°C (0.027 Torr), n = 1.4745. IR spectrum,
D
–1
1
32 56
4
ν, cm : 1732 (C=O). H NMR spectrum, δ, ppm:
0
.82–0.85 (m, 6H, CH ), 0.90–0.92 (m, 6H, CH ),
3
3
(5,7-Dimethyladamantane-1,3-diyl)dimethanediyl
diheptanoate VII. 45 g (50 mL, 0.346 mol) of enanthic
1
.12 (s, 2H, CH Ad), 1.18–1.24 (m, 16H, CH ), 1.51–
2
2
1
.53 (m, 4H, CH ), 1.73–1.74 (m, 8H, CH Ad), 2.13– acid was slowly added dropwise to 124 g (75 mL,
2
2
13
2
.18 (m, 4H, CH ), 2.31 (s, 2H, CH Ad). C NMR 1.042 mol) of thionyl chloride upon reflux. The
2
2
spectrum, δ, ppm: 14.2 (CH ), 22.7 (CH ), 25.1 obtained mixture was heated upon reflux for 30 min,
3
2
and the excess thionyl chloride was evaporated in vac-
uum. About 50 g of enanthoyl chloride was obtained as
a yellow oil. 25 g (0.102 mol) of 5,7-dimethyl-1,3-
bis(hydroxymethyl)adamantane, 70 mL of triethyl-
amine, 50 g (0.337 mol) of enanthoyl chloride, and
(
CH ), 29.0 (CH ), 29.1 (CH ), 31.7 (CH ), 34.7 (C),
2 2 3 2
3
5.6 (CH ), 43.9 (CH ), 46.2 (CH ), 49.5 (CH ),
2 2 2 2
8
1.2 (C), 173.1 (C). Mass spectrum, m/z (I , %):
rel
3
04 (38), 285 (16), 247 (98), 179 (20), 161 (98),
1
20 (60), 106 (30), 57 (100), 43 (48). Found, %: C
2
00 mL of toluene are placed into a three-neck flask
7
4.94; H 10.80. Calculated for C H O , %: C 74.95;
28
48
4
equipped with a mechanical stirrer and a reflux con-
denser. The obtained mixture is heated upon reflux for
H 10.78.
5
,7-Dimethyladamantane-1,3-diyl dinonanoate V
was obtained similarly to diester I from 20 g
0.102 mol) of 5,7-dimethyladamantane-1,3-diol,
8 g (0.30 mol) of pelargonic acid, and 0.85 g
3
h. The formed precipitate of triethylamine hydro-
chloride is filtered off, and the filtrate is evaporated in
vacuum on a rotary evaporator. The residue is purified
via vacuum distillation collecting a fraction with
bp 200–202°C (0.036 Torr). The weight 37 g, yield
(
4
(
0.005 mol, 0.5 mL) of trifluoromethanesulfonic acid
in 200 mL of petroleum ether. The weight of the prod-
uct after the distillation was 22.4 g. The yield 46%,
2
0
–1
7
4%, n = 1.4750. IR spectrum, ν, cm : 1739 (C=O).
D
1
H NMR spectrum, δ, ppm: 0.81–0.85 (m, 12H,
2
0
bp 195–197°C (0.032 Torr), n = 1.4748. IR spec-
D
CH ), 1.06–1.09 (m, 10H, CH Ad, CH ), 1.21–1.29
3
2
2
–1
1
trum, ν, cm : 1732 (C=O). H NMR spectrum, δ,
(
m, 16H, CH Ad, CH ), 2.26 (t, J = 7.32 Hz, 4H,
2 2
ppm: 0.86 (t, J = 6.64 Hz, 6H, CH ), 0.93 (s, 6H,
3
13
CH ), 3.67–3.69 (m, 4H, CH ). C NMR spectrum,
2
2
CH ), 1.14 (s, 2H, CH Ad), 1.22–1.30 (m, 20H, CH ,
3
2
2
δ, ppm: 14.1 (CH ), 22.6 (CH ), 25.0 (CH ),
3
2
2
CH Ad), 1.50–1.57 (m, 4H, CH ), 1.76 (s, 8H, CH ),
2
2
2
2
8.9 (CH ), 30.1 (CH ), 31.2 (C), 31.5 (CH ),
2 3 2
2
.18 (t, J = 7.32 Hz, 4H, CH ), 2.32 (s, 2H, CH ).
2 2
3
4.4 (CH ), 35.5 (C), 39.9 (CH ), 45.1 (CH ), 50.7
1
3
2
2
2
C NMR spectrum, δ, ppm: 14.2 (CH ), 22.7 (CH ),
3
2
(
CH ), 72.9 (CH ), 173.9 (C). Mass spectrum,
2 2
2
2
4
5.2 (CH ), 29.1 (CH ), 29.2 (CH ), 29.20 (CH ),
2 3 2 2
m/z (I , %): 304 (42), 285 (18), 247 (98), 179 (20),
rel
9.3 (CH ), 31.9 (CH ), 34.8 (C), 35.7 (CH ),
2
2
2
1
%
61 (98), 120 (58), 105 (32), 57 (100), 43 (48). Found,
4.0 (CH ), 46.2 (CH ), 49.5 (CH ), 81.2 (C), 173.1
2
2
2
: C 74.98; H 10.75. Calculated for C H O , %:
+
28 48 4
(
C). Mass spectrum, m/z (I , %): 475 [M–1] (<2),
rel
C 74.95; H 10.78.
3
18 (66), 261 (100), 161 (70), 141 (23), 120 (26),
7 (30). Found, %: C 75.57; H 10.96. Calculated for
C H O , %: C 75.58; H 10.99.
5
(5,7-Dimethyladamantane-1,3-diyl)dimethanediyl
dioctanoate VIII was obtained similarly to diester VII
from 30 g (0.134 mol) of 5,7-dimethyl-1,3-
bis(hydroxymethyl)adamantane, 70 mL of triethyl-
amine, 55 g (0.338 mol) of capryloyl chloride, and
30
52
4
5
,7-Dimethyladamantane-1,3-diyl didecanoate VI
was obtained similarly to diester I from 20 g
(
0.102 mol) of 5,7-dimethyladamantane-1,3-diol,
2
00 mL of toluene. The weight of the product after the
5
2.7 g (0.31 mol) of capric acid, and 0.85 g (0.005 mol,
.5 mL) of trifluoromethanesulfonic acid in 200 mL of
distillation was 51 g. The yield 80%, bp 206–208°C
0
2
0
–1
petroleum ether. The weight of the product after the (0.036 Torr), n = 1.4748. IR spectrum, ν, cm : 1739
D
distillation was 23 g. The yield 46%, bp 205–206°C
1
(
C=O). H NMR spectrum, δ, ppm: 0.81–0.84 (m,
2
0
–1
1
2H, CH ), 1.08–1.12 (m, 12H, CH Ad, CH ), 1.21–
(
0.035 Torr), n = 1.4750. IR spectrum, ν, cm : 1732
3
2
2
D
1
1.25 (m, 16H, CH Ad, CH ), 1.54–1.58 (m, 4H,
2 2
(
C=O). H NMR spectrum, δ, ppm: 0.86 (t, J =
.32 Hz, 6H, CH ), 0.93 (s, 6H, CH ), 1.14 (s, 2H, CH ), 2.25 (t, J = 7.36 Hz, 4H, CH ), 3.67–3.68 (m,
2 2
7
3
3
13
CH Ad), 1.20–1.33 (m, 26H, CH , CH Ad), 1.50– 4H, CH ). C NMR spectrum, δ, ppm: 14.1 (CH ),
2
2
2
2
3
1
7
.58 (m, 4H, CH ), 1.76 (s, 6H, CH Ad), 2.18 (t, J = 22.7 (CH ), 25.1 (CH ), 29.00 (CH ), 29.2 (CH ),
2 2
2 2 2 2
13
.32 Hz, 4H, CH ), 2.32 (s, 2H, CH Ad). C NMR 30.1 (CH ), 31.2 (C), 31.8 (CH ), 34.3 (CH ),
2 2
3 2 2
spectrum, δ, ppm: 14.2 (CH ), 22.8 (CH ), 35.5 (C), 39.9 (CH ), 45.4 (CH ), 50.7 (CH ),
3
2
2
2
2
2
2
3
8
3
5.1 (CH ), 29.1 (CH ), 29.2 (CH ), 29.3 (CH ), 72.9 (CH ), 173.9 (C). Mass spectrum, m/z (I , %):
2 3 2 2
2
r
e
l
+
9.4 (CH ), 29.5 (CH ), 31.9 (CH ), 34.7 (C), 477 [M + 1] (<1), 377 (18), 319 (38), 188 (52),
2
2
2
5.7 (CH ), 44.0 (CH ), 46.2 (CH ), 49.5 (CH ), 175 (100), 133 (42), 119 (86), 105 (30), 57 (60), 43 (24).
2
2
2
2
1.2 (C), 173.1 (C). Mass spectrum, m/z (I , %): Found, %: C 75.60; H 10.97. Calculated for
rel
32 (67), 275 (100), 161 (98), 120 (30), 57 (24),
C H O , %: C 75.58; H 10.99.
30 52 4
PETROLEUM CHEMISTRY Vol. 58 No. 8 2018