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4.78 (d, J = 5.6 Hz, 2H), 4.03 (t, J = 6.5 Hz, 2H), 1.90–1.75 (m, 2H), 1.47 (d, J = 7.8 Hz,
2H), 1.42–1.20 (m, 8H), 0.91 (t, J = 6.6 Hz, 3H).
13C NMR (400 MHz, CDCl3) δ 14.14, 22.79, 25.87, 29.04, 29.23, 29.31, 31.74,
68.62,70.74, 100.13, 107.36, 110.35, 120.68, 130.83, 135.58, 158.51, 164.61,165.25.
The procedures for the preparation of 2-(but-3-enyloxy)-4-(octyloxy)benzoic acid (VII,
a yield of 91.5%) were similar to the procedure of compound VI.
FT-IR (KBr, cm−1): 3430, 2930, 2852, 2560, 1650, 1600, 1506, 1452, 1250, 1200,
1150, 1088, 937, 849, 753, 722, 668, 654.
1H NMR (400 MHz, CDCl3) δ 10.88–10.38 (m, 1H), 8.14 (d, J = 8.8 Hz, 1H), 6.65
(dd, J = 8.8, 2.3 Hz, 1H), 6.53 (d, J = 2.2 Hz, 1H), 5.88 (d, J = 6.9 Hz, 1H), 5.31 (d, J =
1.5 Hz, 1H), 5.29–5.21 (m, 1H), 4.28 (t, J = 6.2 Hz, 2H), 4.03 (t, J = 6.5 Hz, 2H), 2.69 (d,
J = 6.6 Hz, 2H), 1.88–1.75 (m, 2H), 1.48 (s, 2H), 1.42–1.23 (m, 8H), 0.91 (t, J = 6.9 Hz,
3H).
13C NMR (400 MHz, CDCl3) δ 14.15, 22.65, 25.96, 29.05, 29.23, 29.31, 31.80, 33.40,
68.59, 68.62, 99.67, 107.08, 110.10, 119.09, 132.94, 135.57, 158.67, 164.58, 165.34.
Synthesis of 4-(4-Propylcyclohexyl)phenyl 2-(allyloxy)-4-(octyloxy)benzoate (X). A solu-
tion of compound VI (8.0 g, 26.14 mmol), 4-(trans-4-propylcyclohexyl)phenol (6.0 g,
27.5 mmol), DCC (7.0 g, 33.4 mmol), 4-PP (0.3 g, 2.03 mmol), and ether (60 ml) was
heated to reflux for 30 h under stirring. After cooling, the precipitate was filtered and
washed with ether. The filtrate was merged and concentrated to give crude product. The
final crude product was purified with column chromatography (silica gel, methylene chlo-
ride/petroleum ether = 12:7) to yield compound X (10.61 g, 80.2%).
FT-IR (KBr, cm−1): 3015, 2938, 2850, 1720, 1600, 1580, 1515, 1459, 1380, 1250,
1200, 1127, 1010, 870, 837, 801, 700, 663.
1H NMR (400 MHz, CDCl3) δ 8.07 (d, J = 8.7 Hz, 1H), 7.25 (d, J = 8.5 Hz, 2H),
7.16–7.08 (m, 2H), 6.61–6.47 (m, 2H), 6.09 (ddt, J = 17.2, 10.5, 4.7 Hz, 1H), 5.59 (dq,
J = 17.2, 1.6 Hz, 1H), 5.30 (dd, J = 10.6, 1.5 Hz, 1H), 4.64 (dt, J = 4.6, 1.6 Hz, 2H),
4.03 (t, J = 6.6 Hz, 2H), 2.65–2.31 (m, 1H), 1.86 (m, 6H), 1.64–1.18 (m, 17H), 1.15–0.98
(m, 2H), 0.92 (m, 6H).
13C NMR (400 MHz, CDCl3) δ 14.16,14.45, 20.07, 22.71, 25.99, 29.12, 29.36, 33.58,
36.99, 39.73, 44.12, 68.35, 69.40, 100.66, 105.59, 111.48, 117.56, 121.62, 127.64, 132.38,
134.47,145.07, 149.01, 160.99, 164.08, 164.28.
Elemental analysis: C33H46O4 requires C78.26, H 9.09; found: C 78.12, H 9.14.
The procedures for the preparation of 4-(4-propylcyclohexyl)phenyl 2-(but-3-
enyloxy)-4-(octyloxy)benzoate (XI) and 4-(2-allyloxy-4-octyloxy benzoate)-4ꢀ-propylbi-
phenyl (XII) were similar to the procedure of compound X.
4-(4-Propylcyclohexyl)phenyl 2-(but-3-enyloxy)-4-(octyloxy)benzoate (XI). Yield: 76.8%.
FT-IR (KBr, cm−1): 3025, 2924, 2860, 1735, 1690, 1601, 1510, 1456, 1360, 1250,
1200, 1150, 1008, 868, 835, 806, 705, 660.
1H NMR (400 MHz, CDCl3) δ 8.03 (d, J = 8.7 Hz, 1H), 7.25 (d, J = 8.4 Hz, 2H),
7.11 (d, J = 8.5 Hz, 2H), 6.52 (d, J = 2.0 Hz, 2H), 6.09–5.87 (m, 1H), 5.23–5.13 (m,
1H), 5.13–5.05 (m, 1H), 4.10 (t, J = 6.7 Hz, 2H), 4.03 (s, 2H), 2.62 (d, J = 6.7 Hz, 1H),
2.54–2.39 (m, 2H), 1.90 (m, 4H), 1.63–1.18 (m, 19H), 1.14–1.02 (m, 2H), 0.90 (m, 6H)
13C NMR (400 MHz, CDCl3) δ 14.10, 14.42, 20.04, 22.66, 25.99, 29.12, 29.22, 29.33,
31.80, 33.50, 34.43, 37.02, 39.73, 44.11, 68.34, 68.45, 100.41, 105.54, 117.16, 121.49,
121.56, 127.64, 131.04, 134.37, 142.23, 144.99, 158.92, 161.29, 164.29.
Elemental analysis: C34H48O4 requires C78.46, H 9.23; found: C 78.41, H 9.30.