J. McNulty et al.
7.4, 7.3 Hz, 2H); 13C NMR (CDCl3, 50 MHz): d=145.0, 135.6, 135.5,
135.4, 135.3, 133.6, 59.3, 42.2 ppm; IR (NaCl): n˜ =2927, 2098, 1604, 1559,
1460 cmÀ1; EIMS (70 eV): m/z (%): 147 (5) [M+], 119 (42), 105 (32), 91
(100); HRMS (EI): m/z calcd for C8H9N3: 147.0875; found: 147.0865.
Bis(2-phenylethyl) benzylamine (Table 1, entries 3 and 6): 1H NMR
(CDCl3, 200 MHz): d=7.21 (m, 15H), 3.76 (s, 2H), 2.81 ppm (s, 8H);
13C NMR (CDCl3, 50 MHz): d=147.5, 147.4, 146.5, 135.7, 135.6, 135.5,
135.4, 135.3 (2C), 135.2 (2C), 135.1 (2C), 135.0 (2C), 133.7, 132.8, 132.7,
65.3, 62.5, 62.4, 40.4, 40.3 ppm; IR (NaCl): n˜ =2929, 1603, 1544, 1454,
503 cmÀ1; EIMS (70 eV): m/z (%): 315 (5) [M+], 224 (10), 206 (10), 191
(40), 149 (5), 120 (8), 105 (100); HRMS (EI): m/z calcd for C23H25N:
315.4581; found: 315.4568.
(70), 57 (100); HRMS (EI) calcd for C11H23O2: 187.1698; found:
187.1682.
Phenylethyl propionate (Table 2, entry 2): 1H NMR (CDCl3, 200 MHz):
d=7.28 (m, 5H), 4.29 (t, J=7.0, 7.0 Hz, 2H), 2.94 (t, J=7.0, 7.0 Hz, 2H),
2.33 (q, J=7.5, 7.5, 7.5 Hz, 2H), 1.12 ppm (t, J=7.5, 7.5 Hz, 3H);
13C NMR (CDCl3, 50 MHz): d=174.3, 137.9, 128.9 (2C), 128.4 (2C),
126.5, 64.7, 35.1, 27.5, 9.1 ppm; IR (NaCl): n˜ =3030, 2349, 1738, 1498,
1384, 1349 cmÀ1; EIMS (70 eV): m/z (%): 178 (10) [M+], 104 (100), 91
(15), 57 (80), 51 (10); HRMS (EI): m/z calcd for C11H14O2: 178.0994;
found: 178.0988.
Octyl benzoate (Table 2, entry 3): 1H NMR (CDCl3, 200 MHz): d=8.06
(d, J=7.4 Hz, 2H), 7.51 (m, 3H), 4.34 (t, J=6.6, 6.6 Hz, 2H), 1.76 (m,
2H), 1.29 (m, 10H), 0.96 ppm (m, 3H); 13C NMR (CDCl3, 50 MHz): d=
164.9, 133.1 (2C), 128.9, 128.7, 127.9, 127.8, 63.4, 31.9, 30.1, 27.6, 27.1,
24.4, 21.0, 12.4 ppm; IR (NaCl): n˜ =2929, 2858, 1719, 1603, 1274,
1113 cmÀ1; EIMS (70 eV): m/z (%): 234 (5) [M+], 123 (100), 105 (90), 77
(75), 70 (20); HRMS (EI): m/z calcd for C15H22O2: 234.1620; found:
234.1609.
2-Nitroethylbenzene (Table 1, entry 9): 1H NMR (CDCl3, 200 MHz): d=
7.26 (m, 5H), 4.61 (t, J=7.3, 7.4 Hz, 2H), 3.32 ppm (t, J=7.4, 7.4 Hz,
2H); 13C NMR (CD3OD, 50 MHz): d=139.5, 128.5 (2C), 127.4 (2C),
126.0, 76.3, 33.4 ppm; IR (NaCl): n˜ =2997, 2881, 1553, 1480, 1443, 1403,
1357 cmÀ1; CIMS (70 eV): m/z (%): 151 (10) [M+], 135 (10), 104 (100),
77.0 (20); HRMS (CI): m/z calcd for C8H9NO2: 151.0633; found:
151.0635 [M+ÀH].
2-Phenylethyl benzoate (Table 2, entry 4): 1H NMR (CDCl3, 200 MHz):
d=8.05 (d, J=7.3 Hz, 2H), 7.43 (m, 8H), 4.55 (t, J=7.0, 6.9 Hz, 2H),
3.09 ppm (t, J=6.9, 6.9 Hz, 2H); 13C NMR (CDCl3, 50 MHz): d=166.4,
137.9, 132.9, 130.3, 129.5 (2C), 128.9 (2C), 128.5 (2C), 128.3 (2C), 127.8,
1-Nitroheptane (Table 1, entry10) : 1H NMR (CDCl3, 200 MHz): d=4.37
(t, J=7.0 Hz, 2H), 2.00 (m, 2H), 1.27 (m, 8H), 0.88 ppm (t, J=6.1,
6.7 Hz, 3H); 13C NMR (CDCl3, 50 MHz): d=75.6, 32.0, 31.5, 29.6, 28.1,
22.6, 14.1 ppm; IR (NaCl): n˜ =2970, 2876, 2829, 1577, 1457, 1350 cmÀ1
;
65.4, 35.2 ppm; IR (NaCl): n˜ =3030, 2966, 2925, 1719, 1603, 1274 cmÀ1
;
CIMS (70 eV): m/z (%): 144 (100) [M+], 128 (10), 45 (20), 31 (10);
HRMS (CI): m/z calcd for C7H14NO2: 144.1025; found: 144.1002
[M+ÀH].
EIMS (70 eV): m/z (%): 234 (100) [M+], 211 (10), 183 (15), 178 (15), 176
(10); HRMS (EI): m/z calcd for C15H14O2: 226.0994; found: 226.0988.
Ethyl 4-nitrobenzoate (Table 2, entry 5): 1H NMR (CDCl3, 200 MHz):
d=8.29 (d, J=9.0 Hz, 2H), 8.21 (d, J=9.0 Hz, 2H), 4.43 (q, J=7.0,
14.1 Hz, 2H), 1.43 ppm (t, J=7.0, 7.1 Hz, 3H); 13C NMR (CDCl3,
50 MHz): d=172.2, 157.4, 142.7, 137.5, 137.4, 130.3, 130.2, 68.8, 21.1 ppm;
IR (NaCl): n˜ =2993, 1717, 1605, 1526, 1474, 1457, 1368 cmÀ1; EIMS
(70 eV): m/z (%): 195 (31) [M+], 166 (42), 150 (100); HRMS (EI): m/z
calcd for C9H9NO4: 195.0532; found: 195.0512.
Isopropyl 4-nitrobenzoate (Table 2, entry 6): 1H NMR (CDCl3,
200 MHz): d=8.28 (d, J=9.1 Hz, 2H), 8.19 (d, J=9.1 Hz, 2H), 5.29 (m,
1H), 1.39 ppm (d, J=6.6 Hz, 6H); 13C NMR (CDCl3, 50 MHz): d=171.0,
157.8, 142.7, 137.5, 137.4, 130.3, 130.2, 76.5, 28.7, 28.6 ppm; IR (NaCl):
n˜ =2988, 1718, 1608, 1529, 1469, 1350 cmÀ1; EIMS (70 eV): m/z (%): 209
(10) [M+], 173 (3), 150 (100); HRMS (EI): m/z calcd for C10H11NO4:
209.2020; found: 209.2010.
Cyclohexyl 4-nitrobenzoate (Table 2, entry 7): 1H NMR (CDCl3,
200 MHz): d=8.28 (d, J=9.2 Hz, 2H), 8.20 (d, J=9.2 Hz, 2H), 5.06 (m,
1H), 1.96 (m, 2H), 1.78 (m, 2H), 1.57 (m, 2H), 1.41 ppm (m, 4H);
13C NMR (CDCl3, 50 MHz): d=170.9, 157.3, 143.2, 137.5, 137.4, 130.3,
130.2, 81.2, 38.4, 38.3, 32.2, 30.5, 30.4 ppm; IR (NaCl): n˜ =2939, 1722,
1608, 1530, 1452, 1349 cmÀ1; EIMS (70 eV): m/z (%): 249 (1) [M+], 233
(1), 194 (1), 168 (8), 150 (50), 120 (30), 104 (86), 82 (100); HRMS (EI):
m/z calcd for C13H15NO4: 249.1001; found: 249.1008.
1-Nitrooctane (Table 1, entry11) : 1H NMR (CDCl3, 200 MHz): d=4.37
(t, J=7.0 Hz, 2H), 1.96 (m, 2H), 1.26 (m, 10H), 0.87 ppm (t, J=6.1,
6.7 Hz, 3H); 13C NMR (CDCl3, 50 MHz): d=75.7, 31.9, 29.6, 28.9, 27.4,
26.2, 22.5, 14.0 ppm; IR (NaCl): n˜ =2925, 2855, 1526, 1465, 1378 cmÀ1
;
CIMS (70 eV): m/z (%): 158 (50) [M+], 124 (10), 74 (70), 45 (100);
HRMS (CI): calcd for C8H16NO2: 158.1181; found: 158.1184 [M+ÀH].
1-Nitrododecane (Table 1, entry12) : 1H NMR (CDCl3, 200 MHz): d=
4.36 (t, J=7.0, 7.0 Hz, 2H), 1.99 (m, 2H), 1.25 (m, 18H), 0.87 ppm (t, J=
6.0, 6.6 Hz, 3H); 13C NMR (CDCl3, 50 MHz): d=75.7, 31.9, 29.7 (3C),
29.5, 29.4, 28.8, 27.4, 26.2, 22.7, 14.1 ppm; IR (NaCl): n˜ =2928, 2855,
1550, 1468, 1380 cmÀ1; CIMS (70 eV): m/z (%): 214 (100) [M+], 198 (15),
177 (5), 45 (10); HRMS (CI): m/z calcd for C12H24NO2: 214.1807; found:
214.1846 [M+ÀH].
1
1-Butoxy-4-iodobenzene (Table 1, entry 14): H NMR (CDCl3, 200 MHz):
d=7.52 (d, J=6.9 Hz, 2H), 6.65 (d, J=6.9 Hz, 2H), 3.90 (t, J=6.3,
6.4 Hz, 2H), 1.75 (m, 2H), 1.45 (m, 2H), 0.87 ppm (t, J=7.2, 7.2 Hz,
3H); 13C NMR (CDCl3, 50 MHz): d=159.0, 138.1 (2C), 116.9 (2C), 82.4,
67.8, 31.2, 19.2, 13.8 ppm; IR (NaCl): n˜ =2960, 2873, 1587, 1572, 1486,
1474, 1283, 1245, 1174, 1000, 819 cmÀ1; CIMS (70 eV): m/z (%): 276 (70)
[M+], 219 (100), 150 (10), 83 (10); HRMS (CI): m/z calcd for C10H13OI:
276.0011; found: 276.0016.
General procedure for esterification (i.e., Table 2)
Ethyl 4-chlorobenzoate (Table 2, entry 8): 1H NMR (CDCl3, 200 MHz):
d=7.99 (d, J=8.4 Hz, 2H), 7.40 (d, J=8.2 Hz, 2H), 4.37 (q, J=7.1,
14.0 Hz, 2H), 1.38 ppm (t, J=7.0, 7.1 Hz, 3H); 13C NMR (CDCl3,
50 MHz): d=166.0, 138.1, 131.1, 131.0, 129.0, 128.8, 128.7, 61.3, 14.4 ppm;
IR (NaCl): n˜ =2927, 1724, 1596, 1461, 1368, 761 cmÀ1; EIMS (70 eV): m/z
(%): 184 (5) [M+], 164 (15), 135 (40), 119 (100); HRMS (EI): m/z calcd
for C9H9ClO2: 184.0291; found: 184.0302.
Isopropyl 4-chlorobenzoate (Table 2, entry 9): 1H NMR (CDCl3,
200 MHz): d=7.97 (d, J=8.7 Hz, 2H), 7.40 (d, J=8.7 Hz, 2H), 5.24 (m,
1H), 1.36 ppm (d, J=6.5 Hz, 6H); 13C NMR (CDCl3, 50 MHz): d=172.0,
146.0, 137.7, 137.6, 136.2, 135.4, 135.3, 75.5, 28.7, 28.6 ppm; IR (NaCl):
n˜ =2983, 1720, 1595, 1469, 1375, 762 cmÀ1; EIMS (70 eV): m/z (%): 198
(5) [M+], 155 (19), 138 (48), 135 (100); HRMS (EI): calcd for
C10H11ClO2: 198.0448; found: 198.0446.
Ethyl 4-bromobenzoate (Table 2, entry 5): 4-Nitrobenzoic acid (40 mg,
0.24 mmol),
Hünigꢁs
base
(0.48 mmol),
and
tetradecyl-
ACHTREUNG
under Ar for 10 min whereupon bromoethane (0.48 mmol) was added.
After analysis by TLC indicated that the reaction was complete (in all
cases within 12 h), the reaction mixture was poured into a methanol/
water (3:2) solution (5 mL) and extracted with n-hexane (35 mL). The
hexane fractions were dried over anhydrous sodium sulfate, diluted with
5% v/v ethyl acetate, and the solution was filtered through a plug of
silica gel. Concentration ofthe ifltrate gave the ester product in 95%
yield. All compounds reported were characterized by using 1H and 13C
NMR spectroscopy as well as MS and high-resolution (HR) MS data.
1
Octyl propionate (Table 2, entry 1): H NMR (CDCl3, 200 MHz): d=4.03
(t, J=6.6, 6.7 Hz, 2H), 3.37 (t, J=6.8, 6.8 Hz, 2H), 2.27 (m, 2H), 1.82
(m, 2H), 1.59 (m, 2H), 1.13 (t, J=6.6, 6.7 Hz, 3H), 1.24 ppm (m, 12H);
13C NMR (CDCl3, 50 MHz): d=174.3, 64.3, 33.7, 32.8, 31.7, 29.1, 28.6,
27.5, 25.8, 22.5, 13.9 ppm; IR (NaCl): n˜ =2958, 2929, 1741, 1465, 1185,
1084 cmÀ1; EIMS (70 eV): m/z (%): 187 (5) [M+], 112 (50), 205 (20), 83
Ethyl 4-methoxybenzoate (Table 2, entry 10): 1H NMR (CDCl3,
200 MHz): d=7.99 (d, J=8.1 Hz, 2H), 6.91 (d, J=8.0 Hz, 2H), 4.33 (q,
J=7.0, 14.1 Hz, 2H), 3.86 (s, 3H), 1.38 ppm (t, J=7.0, 7.1 Hz, 3H);
13C NMR (CDCl3, 50 MHz): d=173.0, 170.0, 138.4, 138.3, 130.0, 120.3,
120.2, 67.5, 62.2, 21.2 ppm; IR (NaCl): n˜ =2982, 1713, 1608, 1512, 1464,
9320
ꢀ 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Chem. Eur. J. 2006, 12, 9314 – 9322