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RSC Advances
Page 9 of 12
Org. Chem. Front
DOI: 10.1039/C6RA22558F
ARTICLE
C14H11NO4, Calculated: C 65.37, H 4.31, O 24.88 ; Found: C Octyl 2-ethylhexanoate, 17: 0.243g, 95% yield, Colourless oil,
65.38, H 4.29, O 24.88.
1H-NMR (400 MHz, CDCl3): δ 4.00 (t, 2H, J=6.4), 2.19 (m, 1H),
Dodecyl 3-nitrobenzoate, 10: 0.275g, 82% yield, Pale yellow 1.55 (m, 2H), 1.53 (m, 2H), 1.38 (m, 2H), 1.34 (m, 2H), 1.32 (m,
oil, 1H-NMR (400 MHz, CDCl3): δ 8.01 (d, 1H, J=8 Hz), 7.47 2H), 1.23 (m, 10H), 0.81 (t, 9H, J=6.8 Hz); 13C-NMR (100 MHz,
(d,1H, J=7.6 Hz), 7.39 (t, 1H, J=7.6 Hz), 7.19 (S, 1H), 3.99 (t, 2H, CDCl3): δ 176.57, 64.14, 47.42, 31.85, 31.76, 31.59, 29.63,
J=6.8 Hz), 2.99(t, 2H, J=7.6 Hz), 2.61 (t, 2H, J=7.6 Hz), 1.53 (m, 29.18, 29.17, 28.68, 25.93, 25.52, 22.62, 14.07, 13.93, 11.85; IR
2H), 1.18 (m, 18H), 0.80 (t, 3H, J=6.8 Hz); 13C-NMR(100 MHz, (KBr pellet, νmax/cm-1) 2950, 2930, 2875, 1740, 1510, 1435,
CDCl3): δ 172.25, 148.36, 14.54, 134.71, 129.36, 123.23, 1025, 850; Elemental analysis for C16H32O2, Calculated: C 74.94,
121.50, 64.95, 35.24, 31.90, 30.43, 29.63, 29.61, 29.55, 29.49, H 12.58; Found: C 74.95, H 12.56.
29.33, 29.21, 28.56, 25.86, 22.68, 14.11; IR (KBr pellet,
νmax/cm-1): 3032, 2987, 2840, 2395, 1723, 1520, 1411, 1370, Dodecyl 2-ethylhexanoate
,
18: 0.281g, 90% yield, Pale yellow
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1068, 793; Elemental analysis for C19H29NO4, Calculated: C oil, H-NMR (400 MHz, CDCl3): δ 4.00 (t, 2H, J=6.8), 2.18 (m,
68.03, H 8.71, O 19.08 ; Found: C 68.02, H 8.73, O 19.05.
1H), 1.61(m, 2H), 1.58 (m, 2H), 1.54 (m, 2H), 1.50 (m, 2H), 1.41
(m, 2H), 1.36 (m, 2H), 1.88 (m, 16H), 0.81 (t, 9H, J=2.4 Hz); 13C-
Phenethyl 4-flurobenzoate, 11: 0.227g, 93 %yield, Pale yellow NMR (100 MHz, CDCl3): δ 176.57, 64.15, 47.43, 31.91, 31.85,
oil, 1H-NMR (300 MHz, CDCl3): δ 8.03 (d, 2H, J=2.1 Hz), 7.35 (t, 29.64, 29.63, 29.56, 29.53, 29.34, 29.22, 28.69, 25.94, 25.53,
1H, J=1.5 Hz), 7.32 (t, 1H, J=1.5 Hz), 7.30 (d, 1H, J=2.7 Hz), 7.27 22.68, 22.64, 14.11, 13.95, 11.86; IR (KBr pellet, νmax/cm-1)
(d, 1H, J=2.7 Hz), 7.08 (d, 2H, J=1.19 Hz), 7.06 (t, 1H, J=2.7 Hz), 2965, 2879, 1743, 1523, 1390, 1005, 790; Elemental analysis
4.52 (t, 2H, J=6.9 Hz), 3.07 (t, 2H, J=6.9 Hz); 13C-NMR (75 MHz, for C20H40O2, Calculated: C 76.86, H 12.90; Found: C 76.87, H
CDCl3): δ167.63, 165.76, 138.01, 132.36, 129.15, 128.78, 12.88.
128.54, 126.85, 126.70, 115.86, 115.56, 65.79, 35.42;IR (KBr
pellet, νmax/cm-1): 3080, 3025, 2948, 2860, 1720, 1560, 1405, Sec-butyl-2-ethylhexanoate, 19: 0.186g, 93% yield, Colourless
1270, 1080, 760; Elemental analysis for C15H13FO2, Calculated: oil, 1H-NMR (400 MHz, CDCl3): δ 4.86 (m, 1H), 2.22 (m, 1H),
C 73.76, H 5.36, O 13.10 ; Found: C 73.76, H 5.35, O 13.09.
1.58 (m, 2H), 1.49 (m, 4H), 1.20 (m, 4H), 1.07 (d, 3H, J=6.4 Hz),
0.89 (t, 9H, J=3.6 Hz); 13C-NMR (100 MHz, CDCl3): δ 176.17,
Octadecyl 4-flurobenzoate, 12: 0.357g, 91% yield, White solid, 71.71, 47.67, 33.29, 31.87, 29.29, 25.66, 22.61, 19.63, 13.95,
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mp 38-40 °
C, H-NMR (400 MHz, CDCl3): δ 8.06 (dd, 2H, J=2.4 11.86, 9.78; IR (KBr pellet, νmax/cm-1) 2915, 2894, 2315, 1712,
Hz), 7.10 (dd, 2H, J= 8.8 Hz), 4.3 (t, 2H, J=6.8 Hz), 1.75 (m, 2H), 1487, 1075, 863; Elemental analysis for C12H24O2, Calculated: C
1.59 (m, 2H), 1.41 (m, 4H), 1.35 (m, 24H), 0.87 (t,3H, J=6.8 Hz); 71.95, H 12.08; Found: C 71.97, H 12.05.
13C-NMR (100 MHz, CDCl3): δ 165.74, 132.09, 132, 126.74,
126.71, 115.55, 115.32, 65.30, 31.93, 29.70, 29.65, 29.58, (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-ethylhexanoate,
29.53, 29.37, 29.29, 28.68, 26.02, 22.70, 14.14; IR (KBr pellet, 20: 0.245g, 87% yield, Pale yellow oil, 1H-NMR (400 MHz,
νmax/cm-1): 3045, 2990, 2866, 2310, 1732, 1520, 1436, 1035. CDCl3): δ 1.98 (m, 1H), 1.91 (m, 2H), 1.69 (t, 1H, J=3.2 Hz), 1.66
826; Elemental analysis for C25H41FO2, Calculated: C 76.48, H (m, 6H), 1.59 (m, 2H), 1.55 (m, 1H), 1.50 (m, 1H), 1.41 (m, 1H),
10.53, O 8.15 ; Found: C 76.50, H 10.53, O 8.14.
1.39 (m, 1H), 1.36 (m, 1H), 1.31 (m, 2H), 1.25 (m, 2H), 0.89 (t,
6H, J=6.8 Hz), 0.82 (d, 3H, J=4 Hz), 0.75 (d, 6H, J=6.8 Hz); 13C-
Phenethyl 4-chlorobenzoate, 14: 0.281g, 84% yield, Pale NMR (100 MHz, CDCl3): δ 175.97, 73.76, 47.91, 46.91, 40.87,
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yellow oil, H-NMR (400 MHz, CDCl3): δ 7.75 (d, 2H, J=7.6 Hz), 34.29, 32.13, 31.36, 29.62, 25.94, 25.57, 24.60, 23.07, 22.60,
7.42 (t, 2H, J=7.6 Hz), 7.39 (d, 2H, J=7.6 Hz), 7.32 (t, 1H, J=7.2 22.04, 20.81, 13.94, 11.89; Elemental analysis for C18H34O2,
Hz), 7.29 (d, 2H, J=6.8 Hz), 4.55 (t, 2H, J=7.2 Hz), 3.08 (t, 2H, Calculated: C 76.54, H 12.13; Found: C 76.55, H 12.11.
J=6.8 Hz); 13C-NMR (100 MHz, CDCl3): δ 165.62, 137.65, 133.73,
132.54, 131.39, 131.08, 130.10, 128.99, 128.69, 128.57, Dodecyl-4-methylbenzoate, 21: 0.277g, 91% yield, Colourless
126.66, 126.56, 66.02, 35.06; IR (KBr pellet, νmax/cm-1): 3048, oil, 1H-NMR (400 MHz, CDCl3): δ 7.86 (d, 2H, J=7.6 Hz), 7.15 (d,
2987, 2829, 2356, 1747, 1510, 1435, 1112, 1005, 860; 2H, J=7.59 Hz), 4.21 (t, 2H, J=6.4 Hz), 2.314 (S, 3H), 1.670
Elemental analysis for C15H13ClO2, Calculated: C 69.10, H 5.03, (m,2H), 1.349 (m, 18H), 0.797(t, 3H, J=6Hz); 13C-NMR (100
O 12.27 ; Found: C 69.11, H 5.01, O 12.27.
MHz, CDCl3): δ 166.79, 143.39, 134.63, 132.07, 129.16, 128.28,
127.18, 64.97, 31.93, 29.65, 29.60, 29.55, 29.37, 29.30, 28.73,
Phenethyl propionate, 16: 0.163g, 92% yield, Pale yellow oil, 26.06, 22.7, 21.63, 14.13; IR (KBr pellet, νmax/cm-1) 3020, 2842,
1H-NMR (400 MHz, CDCl3): δ 7.21 (m, 4H), 7.13 (t, 1H, J=7.2 2336, 1740, 1486, 1100, 910; Elemental analysis for C20H32O2,
Hz), 4.19 (t, 2H, J=7.2 Hz), 2.84 (t, 2H, J=6.8 Hz), 2.02 (m, 2H), Calculated: C 78.90, H 10.59; Found: C 78.89, H 10.60.
1.02 (t, 3H, J=7.6 Hz); 13C-NMR (100 MHz, CDCl3): δ 174.42,
128.94, 128.65, 128.49, 128.34, 126.87, 126.55, 64.96, 35.36, Phenethyl 4-methylbenzoate, 22: 0.197g, 93% yield, Pale
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27.58, 9.12; IR (KBr pellet, νmax/cm-1): 2930, 2882, 2345, 1747, yellow oil, H-NMR (400 MHz, CDCl3): δ 7.91 (d, 4H, J=7.6 Hz),
1426, 1020, 796; Elemental analysis for C11H14O2, Calculated: C 7.33 (d, 2H, J=7.6 Hz), 7.29 (t, 2H, J=6.8 Hz), 7.23 (t, 1H, J=6.4
74.13, H 7.92; Found: C 74.13, H 7.91.
Hz), 4.5 (t, 2H, J=10.4 Hz), 3.07 (t, 2H, J=6.8 Hz), 2.39 (S, 3H);
13C-NMR (100 MHz, CDCl3): δ 166.63, 143.60, 137.99, 129.59,
129.08, 128.99, 128.53, 127.51, 126.56, 65.33, 35.26, 21.68; IR
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Org. Chem. Front., 2016, 00, 1-11 | 9
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