1602
RASKIL’DINA et al.
Table 4. Spectral and physicochemical characteristics of the synthesized compounds
Mass spectrum,
Compound
Yield, %
88
NMR (CDCl3, δ, ppm)
m/z (Irel, %)
5-Ethyl-5-[(benzyloxy)methyl]-
2,2-dimethyl-1,3-dioxane (7b),
colorless liquid, Тb 163°С
(5 mmHg)
1H NMR spectrum (C6D6, δ, ppm, J, Hz): 0.65 s M+ = 249 (32), 206 (12),
(3Н, С2″Н3), 1.26 m (2Н, С1″H2), 1.29 s (3Н, 120 (4), 107 (8), 91 (100),
С1′Н3), 1.40 s (3Н, С2′Н3), 3.41 s (2Н, С7Н2), 81 (2), 70 (4), 59 (8), 43 (9)
3.45 d (2Н, С4Н2), 3.68 d (2Н, С6Н2), 4.28 s (2Н,
С8Н2), 7.10 m (5Н, Ph-). 13C NMR spectrum
(C6D6, δ, ppm): 7.29 (С2″), 21.34 (C2′), 24.50
(C1″), 26.71 (C1′), 36.91 (C5), 65.45 (C4 + C6),
70.40 (C7), 73.46 (C8), 98.07 (C2), 127.58,
127.70, 128.00, 128.32, 128.48, 139.24 (Ph)
3-Allyloxypropane-1,2-diol
(8а), colorless liquid,
Тb 108°С (5 mmHg)
92
1H NMR spectrum (CDCl3, δ, ppm, J, Hz): M+ = 132 (none), 101 (6),
3.42–3.53 m (2H, C1Ha, C3Ha), 3.70–3.90 m 84 (8), 71 (19), 61 (35), 43
(3H, C3Hb, C2H, C1Hb), 4.02 d (2H, C4Ha, (48), 41 (100)
C4Hb), 4.35 s (2-OH), 5.13 d.d (1Н, C6Ha, 2J =
1.5, 3J = 10.4), 5.23 d.d (1H, C6Hb, 2J = 1.6, 3J =
17.3), 5.82–5.94 m (1H, C5H)
3-(Benzyloxy)propan-1,2-diol
(8b), colorless liquid,
Тb 192°С (5 mmHg)
88
90
1H NMR spectrum (CDCl3, δ, ppm, J, Hz): M+ = 182 (6), 107 (38), 79
3.27 s (2-ОH), 3.35–3.62 m (3H, C1Ha, C3Ha, (7), 65 (9), 43 (2)
C3Hb), 3.75 m (1H, C1Hb), 4.20 m (C2H), 4.31 m
(2Н, C4Ha, C4Hb), 7.00–7.21 m (5H, Ar)
4-(Allyloxy)butane-1,2-diol
(9а), colorless liquid,
Тb 134°С (5 mmHg)
1H NMR spectrum (CDCl3, δ, ppm, J, Hz): 1.71 M+ = 147 (2), 115 (44), 97
d (2Н, С3Н2), 3.50 m (1Н, С2Н), 3.61 s (2Н, (4), 87 (21), 71 (60), 57
С4H2), 3.75 d (2Н, С1Н2), 3.87 m (2Н, НО–С1– (51), 41 (100)
С2–ОН), 4.02 s (2Н, С6H2), 5.17 d.d (2Н, С8Н2),
5.88 m (1Н, С7Н). 13C NMR spectrum (CDCl3,
δ, ppm): 32.70 (С3), 66.40 (С4), 67.56 (С1),
70.57 (С2), 71.85 (С6), 117.06 (С8), 134.29 (С7)
2-[(Allyloxy)methyl]-2-
ethylpropane-1,3-diol (10а),
colorless liquid, Тb 153°С
(5 mmHg)
80
1H NMR spectrum (C6D6, δ, ppm, J, Hz): 0.78 s M+ = 175 (2), 117 (7), 99
(3Н, С3′Н3), 1.35 d (2Н, С2′Н2), 3.40 d.d (4Н, (12), 86 (36), 71 (43), 54
С1Н2, С3Н2), 3.60 d (2Н, С4′Н2), 3.75 d (2Н, (81), 41 (100)
С5′Н2), 5.05 d (2Н, С7′Н2), 5.72 m (1Н, С6′Н).
13C NMR spectrum (C6D6, δ, ppm): 7.78 (С3′),
22.96 (C2′), 43.37 (C2), 65.37 (C1 + C3), 72.48
(C4′+C5′), 116.49 (C7′)
2-[(Benzyloxy)methyl]-2-
ethylpropane-1,3-diol (10b),
colorless liquid, Тb 213°С
(5 mmHg)
60
1H NMR spectrum (C6D6, δ, ppm, J, Hz): 0.82 s M+ = 107 (31), 91 (100), 72
(3Н, С2″Н3), 1.39 m (2Н, С1″Н2), 3.35 s (2Н, (16), 57 (12), 41 (9)
С1′Н2), 3.68 d.d (4Н, С1Н2, С3Н2), 4.30 s (2Н,
С2′Н2), 7.10 m (5Н, Ph). 13С NMR spectrum
(C6D6, δ, ppm): 7.49 (C2″), 22.67 (C1″), 43.15
(C2), 65.13 (C1 + C3), 72,12 (C1′), 73,35 (C2′),
126.44, 127.43, 127.49, 127.74, 128.07, 138.60
(Ph)
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 88 No. 10 2015