6
Tetrahedron
ACCEPTED MANUSCRIPT
(m, 2H), 1.46 – 1.36 (m, 4H), 0.93 (t, J = 7.0 Hz, 3H).13C NMR
4.3.43. Isobuthyl 4-nitrobenzoate (4o) 30. Pale yellow oil; 51%
1
(125 MHz, CDCl3) δ 166.43, 132.51, 130.30, 129.27, 128.05,
64.86, 28.18, 27.95, 22.10, 13.72.
Yield. H NMR (500 MHz, CDCl3) δ 8.29 (d, J = 8.7 Hz, 2H),
8.21 (d, J = 8.7 Hz, 2H), 4.16 (d, J = 6.7 Hz, 2H), 2.11 (m, 1H),
1.04 (d, J = 6.8 Hz, 6H). 13C NMR (125 MHz, CDCl3) δ 164.42,
150.25, 135.62, 130.37, 123.26, 71.62, 27.58, 18.86.
4.3.34. Octyl benzoate (4f)18. Colorless oil; 54% Yield. 1H NMR
(500 MHz, CDCl3) δ 8.05 (d, J = 7.3 Hz, 2H), 7.55 (t, J = 7.4 Hz,
1H), 7.44 (t, J = 7.8 Hz, 2H), 4.32 (t, J = 6.7 Hz, 2H), 1.81 – 1.73
(m, 2H), 1.48 – 1.41 (m, 2H), 1.38 – 1.27 (m, 8H), 0.89 (t, J =
6.9 Hz, 3H). 13C NMR (125 MHz, CDCl3) δ 166.39, 132.49,
130.31, 129.27, 128.03, 64.86, 31.54, 28.99, 28.95, 28.48, 25.80,
22.38, 13.82.
4.3.35. Ethyl 3-methylbenzoate (4g)28. Colorless oil; 82% Yield.
1H NMR (500 MHz, CDCl3) δ 7.85 (m, 2H), 7.33 (m, 2H), 4.37
(q, J = 7.1 Hz, 2H), 2.40 (s, 3H), 1.39 (t, J = 7.1 Hz, 3H). 13C
NMR (125 MHz, CDCl3) δ 166.50, 137.78, 133.26, 130.20,
129.78, 127.92, 126.40, 60.56, 20.95, 14.05.
4.3.36. Ethyl 4-nitrobenzoate (4h)16k. Pale yellow oil; 69% Yield.
1H NMR (500 MHz, CDCl3) δ 8.28 (d, J = 8.8 Hz, 2H), 8.21 (d, J
= 8.8 Hz, 2H), 4.44 (q, J = 7.1 Hz, 2H), 1.43 (t, J = 7.1 Hz, 3H).
13C NMR (125 MHz, CDCl3) δ 164.42, 150.23, 135.60, 130.39,
123.23, 61.69, 13.96.
4.3.44. Isobuthyl 2-naphthoate (4p)31. Colorless oil; 65% Yield.
1H NMR (500 MHz, CDCl3) δ 8.63 (s, 1H), 8.09 (dd, J = 8.6, 1.5
Hz, 1H), 7.97 (d, J = 8.1 Hz, 1H), 7.88 (d, J = 8.8 Hz, 2H), 7.56
(m, 2H), 4.19 (d, J = 6.6 Hz, 2H), 2.16 (m, 1H), 1.08 (d, J = 6.7
Hz, 6H). 13C NMR (125 MHz, CDCl3) δ 165.75, 134.47, 131.49,
129.89, 128.30, 127.08,126.72, 125.55, 124.76, 124.22, 70.12,
26.94, 18.22.
4.3.45. Cyclopropylmethyl benzoate (4q)9. Colorless oil; 76%
Yield. H NMR (500 MHz, CDCl3) δ 8.07 (d, J = 7.1 Hz, 2H),
7.55 (t, J = 7.4 Hz, 1H), 7.44 (t, J = 7.7 Hz, 2H), 4.16 (d, J = 7.2
Hz, 2H), 1.31 – 1.22 (m, 1H), 0.62 (q, J = 6.0 Hz, 2H), 0.37 (q, J
= 4.7 Hz, 2H). 13C NMR (125 MHz, CDCl3) δ 166.47, 132.53,
130.30, 129.33, 128.04, 69.4, 9.66 , 3.03.
1
4.3.46. Cyclopropylmethyl [1,1'-biphenyl]-4-carboxylate (4r)16h
.
1
Colorless oil; 63% Yield. H NMR (500 MHz, CDCl3) δ 8.15 (d,
J = 8.5 Hz, 2H), 7.67 (d, J = 8.5 Hz, 2H), 7.63 (d, J = 7.1 Hz,
2H), 7.47 (t, J = 7.5 Hz, 2H), 7.40 (t, J = 7.4 Hz, 1H), 4.19 (d, J =
7.2 Hz, 2H), 1.30 (m, 1H), 0.64 (q, J = 6.0 Hz, 2H), 0.40 (q, J =
4.7 Hz, 2H). 13C NMR (125 MHz, CDCl3) δ 166.37, 145.30,
139.83, 129.89, 129.07, 128.68, 127.86, 127.04, 126.76, 69.44,
9.74, 3.09.
4.3.47. 4-Methylbenzaldehyde (2d'). Colorless oil; 88% Yield. 1H
NMR (500 MHz, CDCl3) δ 9.96 (s, 1H), 7.78 (d, J = 8.1 Hz, 2H),
7.33 (d, J = 8.0 Hz, 2H), 2.44 (s, 3H). 13C NMR (125 MHz,
CDCl3) δ 191.71, 145.27, 133.94, 129.56, 129.43, 21.56.
4.3.37. Propyl 3-methylbenzoate (4i). Colorless oil; 73% Yield.
1H NMR (500 MHz, CDCl3) δ 7.85 (d, J = 9.6 Hz, 2H), 7.34 (m,
2H), 4.28 (t, J = 6.7 Hz, 2H), 2.40 (s, 3H), 1.79 (m, 2H), 1.04 (t,
J = 7.4 Hz, 3H). 13C NMR (125 MHz, CDCl3) δ 166.57, 137.80,
133.27, 130.21, 129.79, 127.94, 126.41, 66.18, 21.87, 20.98,
10.25. HRMS calcd for C11H14O2[M+H]+, 178.0994; found,
178.0991.
4.3.38. Propyl 4-methoxybenzoate (4j)29. Colorless oil; 78%
Yield. H NMR (500 MHz, CDCl3) δ 8.00 (d, J = 8.9 Hz, 2H),
6.91 (d, J = 8.9 Hz, 2H), 4.25 (t, J = 6.7 Hz, 2H), 3.85 (s, 3H),
1.81 – 1.74 (m, 2H), 1.02 (t, J = 7.4 Hz, 3H). 13C NMR (125
MHz, CDCl3) δ 166.16, 162.99, 131.26, 122.71, 113.28, 65.95,
55.11, 21.90, 10.26.
1
Acknowledgments
4.3.39. Butyl 4-methylbenzoate (4k)16i. Colorless oil; 70% Yield.
1H NMR (500 MHz, CDCl3) δ 7.93 (d, J = 8.2 Hz, 2H), 7.23 (d, J
= 8.0 Hz, 2H), 4.31 (t, J = 6.6 Hz, 2H), 2.40 (s, 3H), 1.78 – 1.71
(m, 2H), 1.51 – 1.44 (m, 2H), 0.98 (t, J = 7.4 Hz, 3H). 13C NMR
(125 MHz, CDCl3) δ 165.71, 142.34, 128.53, 127.98, 126.79,
63.59, 29.79, 20.57, 18.26, 12.73.
Acknowledgments should be inserted at the end of the paper,
before the references, not as a footnote to the title. Use the
unnumbered Acknowledgements Head style for the
Acknowledgments heading.
References
4.3.40. Isobutyl benzoate (4l)18. Colorless oil; 75% Yield. H
1
1. (a)Otera, J.; Nishikido, J. Esterification: methods, reactions, and
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NMR (500 MHz, CDCl3) δ 8.06 (d, J = 7.0 Hz, 2H), 7.55 (t, J =
7.4 Hz, 1H), 7.44 (t, J = 7.7 Hz, 2H), 4.11 (d, J = 6.6 Hz, 2H),
2.09 (m, 1H), 1.03 (d, J = 6.7 Hz, 6H). 13C NMR (125 MHz,
CDCl3) δ 165.55, 131.75, 129.50, 128.48, 127.28, 69.94, 26.87,
18.14.
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4.3.41. Isobutyl 3-methylbenzoate (4m). Colorless oil; 61% Yield.
1H NMR (500 MHz, CDCl3) δ 7.85 (d, J = 8.5 Hz, 2H), 7.34 (m,
2H), 4.10 (d, J = 6.6 Hz, 2H), 2.41 (s, 3H), 2.09 (m, 1H), 1.03 (d,
J = 6.7 Hz, 6H). 13C NMR (125 MHz, CDCl3) δ 166.56, 137.84,
133.30, 130.22, 129.80, 127.96, 126.40, 70.69, 27.66, 21.02,
18.95. HRMS calcd for C12H16O2[M+H]+, 192.1150; found,
192.1142.
4.3.42. Isobuthyl 3,5-dimethoxybenzoate (4n). Colorless oil; 72%
1
Yield. H NMR (500 MHz, CDCl3) δ 7.19 (d, J = 2.4 Hz, 2H),
6.64 (t, J = 2.4 Hz, 1H), 4.09 (d, J = 6.6 Hz, 2H), 3.82 (s, 6H),
2.07 (m, 1H), 1.01 (d, J = 6.7 Hz, 6H). 13C NMR (125 MHz,
CDCl3) δ 166.03, 160.36, 132.13, 106.90, 105.05, 70.84, 55.20,
27.61, 18.89. HRMS calcd for C13H18O4[M+H]+, 238.1205;
found, 238.1209.
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