SYNTHESIS OF BENZYL ALKYL ETHERS BY INTERMOLECULAR DEHYDRATION
1153
9
8
NMR spectrum, δ, ppm: 15.25 (С ), 65.74 (С ), 72.14
(3Н, СНСН , J 7.5 Hz), 1.23 d (3H, СН СН , J 7.5 Hz),
3
2
3
7
4
3,5
2,6
(
(
(
С ), 127.67 (С ), 127.82 (С ), 128.43 (С ), 138.29
С ). Mass spectrum, m/z (I , %): 136 (10) [М] , 102
15), 91 (100), 79 (37), 77 (20), 65 (20), 63 (5), 59 (7),
1.45–1.75 m (2Н, СНСН СН ), 3.45–3.55 m (1Н,
2 3
1
+
А
СН СНСН СН ), 4.51 (1Н , СН , J 12 Hz), 4.60
3 2 3 2
rel
В
13
(1Н , СН , J 11.5 Hz), 7.25–7.50 m (5Н, СН ). С
2 arom
1
1
8
5
1 (12), 39 (15).
NMR spectrum, δ, ppm: 9.86 (C ), 19.20 (C ), 29.23
1
0
9
7
4
(
(
C ), 70.29 (C ), 76.22 (C ), 127.37 (C ), 127.63
Benzyl propyl ether (3c). Yield 91% (а), 80% (b),
colorless liquid, bp 90–91°С (20 mmHg) {bp 205–
08°С (760 mmHg) [13]}. H NMR spectrum, δ, ppm:
.07 t (3H, СН , J 7.6 Hz), 1.65–1.85 m (2H,
2
,6
3,5
1
C ), 128.32 (C ), 139.21 (C ). Mass spectrum, m/z
+
1
(Irel, %):164 (2) [М] , 135 (19), 108 (4), 107 (6), 92
2
1
(
40), 91 (100), 79 (9), 77 (6), 65 (12), 41 (5).
3
Benzyl tert-butyl ether (3h). Yield 50% (a), 50%
СH СH СH ), 3.54 t (2H, СH СH СH , J 6.4 Hz), 4.61
2
2
3
2
2
3
1
3
(
2
1
(
(
(
(
(
b), colorless liquid, bp 80–82°С (10 mmHg) {bp 204–
08°C (760 mmHg) [13]}. H NMR spectrum, δ, ppm:
s (2Н, СH O), 7.25–7.55 m (5H, СН ). C NMR
spectrum, δ, ppm: 10.75 (С ), 23.09 (С ), 72.86 (С ),
2.89 (С ), 127.54 (С ), 127.68 (С ), 128.42 (С ),
2
arom
9
1
1
0
8
7
4
3,5
2,6
.21 s (9Н, СН ), 4.57 s (2H, СН О), 7.20–7.50 m
7
1
3
2
1
3
1
5H, СНarom). С NMR spectrum, δ, ppm: 27.81
38.85 (С ).
9
,10,11
7
8
4
С
), 64.27 (С ), 73.64 (С ), 127.26 (С ), 127.78
Benzyl 2-propyl ether (3d). Yield 85% (a), 65%
b), colorless liquid, bp 68–70°С (10 mmHg) {bp 78–
1°С (15 mmHg) [13]}. H NMR spectrum, δ, ppm: 1.28
d (6H, СH , J 6 Hz), 3.60–3.80 m [1H, СН(CH ) ],
.56 s (2Н, СH O), 7.25–7.60 m (5H, СНarom).
NMR spectrum, δ, ppm: 22.15 (С ), 70.06 (С ),
0.97 (С ), 128.39 (С ), 127.58 (С ), 128.36 (С ),
2,6
3,5
1
С ), 128.40 (С ), 139.94 (С ). Mass spectrum, m/z
(
8
+
I , %): 164 (4) [М] , 149 (18), 131 (5), 108 (16), 107
1
rel
14), 92 (8), 91 (100), 79 (16), 77 (9), 57 (17).
3
3 2
1
3
Benzyl pentyl ether (3i). Yield 75% (а), 60% (b),
4
С
2
9
,10
7
yellowish liquid, bp 107–108°С (10 mmHg) {bp 116–
1
8
4
3,5
2,6
117°С (17 mmHg) [16]}. H NMR spectrum, δ, ppm:
7
1
1
0.94 t (3H, СН , J 7.2 Hz), 1.30–1.80 m [6H,
3
39.14 (С ).
СH (СH ) СH ], 3.51 t (2H, OСН CH , J 6.4 Hz), 4.54
2
2 3
3
2
2
1
3
Benzyl butyl ether (3e). Yield 91% (a), 55% (b),
colorless liquid, bp 90–92°С (10 mmHg) {bp 95–97°С
15 mmHg) [13]}. H NMR spectrum, δ, ppm: 0.99 t
3H, СН , J 7.6 Hz), 1.40–1.55 m (2H, СH СH ), 1.60–
s (2Н, СH O), 7.25–7.43 m (5H, СН ). С NMR
spectrum, δ, ppm: 14.06 (С ), 22.57 (С ), 28.41 (С ),
2
arom
11
1
2
10
1
9
8
7
4
(
2
9.50 (С ), 70.55 (С ), 72.88 (С ), 127.46 (С ), 127.62
3
,5
2,6
1
(
3
2
3
(С ), 128.35 (С ), 138.77 (С ).
1
6
.75 m (2H, СH CH CH ), 3.52 t (2H, OСН CH , J
2 2 3 2 2
Benzyl cyclopentyl ether (3j). Yield 55% (а), 36%
(b), colorless liquid, bp 86–88°C (2 mmHg) {bp 116–
.8 Hz), 4.54 s (2Н, СH O), 7.25–7.55 m (5H, СН ).
С NMR spectrum, δ, ppm: 13.94 (C ), 19.42 (C ),
1.89 (C ), 70.22 (C ), 72.87 (C ), 127.48 (C ), 127.63
C ), 128.34 (C ), 138.74 (C ). Mass spectrum, m/z
2
arom
10
1
3
11
1
9
8
7
4
117°C (10 mmHg) [17]}. H NMR spectrum, δ, ppm:
3
(
(
2
,6
3,5
1
1.24–1.89 m (8H, СH
(2Н, СН О), 7.12–7.66 m (5H, СНarom). С NMR
spectrum, δ, ppm: 23.68 (С ), 32.34 (С ), 70.72
2
), 3.84–4.03 m (1Н, CH), 4.57 s
1
3
+
2
I , %): 164 (3) [M] , 108 (8), 107 (9), 93 (5), 92 (70),
rel
10,11
9,12
2,6
9
1 (100), 79 (11), 77 (6), 65 (12).
7
8
4
(
С ), 80.95 (С ), 127.33 (С ), 127.64 (С ), 128.41
(С ), 138.31 (С ).
3
,5
1
Benzyl 2-butyl ether (3f). Yield 69% (а), 52% (b),
colorless liquid, bp 84–86°C (10 mmHg) {bp 79–79.5°C
Benzyl hexyl ether (3k). Yield 68% (а), 61% (b),
yellowish liquid, bp 120–122°С (10 mmHg) {bp 106–
107°С (6 mmHg) [17]}. H NMR spectrum, δ, ppm:
1
(
(
16 mmHg) [14]}. H NMR spectrum, δ, ppm: 1.08 t
3Н, СН СН , J 8 Hz), 1.33 d (3H, СНСН , J 4 Hz),
1
2
3
3
1
.57–1.83 m (2Н, СНСН СН ), 3.50–3.63 m [1Н,
2 3
1.08 t (3H, СН , J 7.3 Hz), 1.35–1.86 m [8H,
3
СН(CH )СН СН ], 4.67 s (2H, СН О), 7.35–7.50 m
3
2
3
2
СH (СH ) СH ], 3.60 t (2H, OСН CH , J 6.3 Hz), 4.55
2
2 4
3
2
2
1
3
11
1
3
(
1
(
5Н, СН ). С NMR spectrum, δ, ppm: 9.81 (C ),
9.13 (C ), 28.40 (C ), 70.21 (C ), 72.03 (C ), 127.33
C ), 127.57 (C ), 128.26 (C ), 139.11 (C ). Mass
spectrum, m/z (I , %): 164 (21) [M] , 135 (7), 108 (5),
arom
8
s (2Н, СH O), 7.31–7.49 m (5H, СН ). С NMR
spectrum, δ, ppm: 14.15 (С ), 22.76 (С ), 26.06 (С ),
9.92 (C ), 31.87 (С ), 70.51 (C ), 72.93 (С ), 127.42
(C ), 127.47 (С ), 128.37 (C ), 138.89 (C ).
2
arom
12
10
9
7
1
3
11
4
2,6
3,5
1
1
0
9
8
7
2
+
4
3,5
2,6
1
rel
9
2 (42), 91 (100), 79 (16), 77 (14), 65 (29), 51 (11), 43
Benzyl cyclohexyl ether (3l). Yield 73% (а), 49%
(
6), 41 (14).
(
b), yellowish liquid, bp 140–142°C (15 mmHg) {bp
1
(
S)-(+)-2-Butyl benzyl ether (3g). Yield 44% (а),
122–124°C (0.1 mmHg) [18]}. H NMR spectrum, δ,
ppm: 1.20–2.20 m (10H, СH ), 3.30–3.45 m (1Н, СH),
4.60 s (2Н, СH O), 7.25–7.45 m (5H, СНarom).
colorless liquid, bp 72–74°C (6 mmHg) {bp 50°С
2
1
13
(
0.2 mmHg) [15]}. H NMR spectrum, δ, ppm: 0.96 t
2
С
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 54 No. 8 2018