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The Journal of Organic Chemistry
(3-Bromophenyl)methanol (2f): The product (61.8 mg, 66%
as yellow oil. 1H NMR (600 MHz, CDCl3) δ 7.24-7.19 (m,
2H), 7.17 – 7.10 (m, 2H), 4.85 (q, J = 6.5 Hz, 1H), 2.34 (s,
3H), 2.32 (br, 1H), 1.47 (d, J = 6.4 Hz, 3H); HRMS (ESI-
TOF) m/z: [M+H-H2O]+ Calcd for C9H11: 119.0855; found:
119.0861. FTIR (KBr): 3422, 2959, 1514, 1365, 1208, 1081,
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8
yield) was isolated using flash chromatography (25%
1
EtOAc/PE), as colorless oil. H NMR (400 MHz, CDCl3) δ
7.52 (d, J = 1.8 Hz, 1H), 7.53-7.40 (m, 1H), 7.30 – 7.26 (m,
1H), 7.24-7.20 (m, 1H), 4.66 (d, J = 4.3 Hz, 2H), 1.95 (br,
1H); 13C{1H} NMR (101 MHz, CDCl3) δ 143.1, 130.6, 130.1,
129.9, 125.3, 122.6, 64.5; HRMS (ESI-TOF) m/z: [M+H-
H2O]+ Calcd for C7H6Br: 168.9647; found: 168.9645. FTIR
(KBr): 3319, 2924, 2871, 1596, 1569, 1472, 1428, 1352, 1200,
1091, 1069, 1019, 880, 825, 784, 696, 666, 612, 517 cm-1.
Analytical data is in accordance with literature data. 12
819 cm-1. Analytical data is in accordance with literature data.
15
1-(4-Isobutylphenyl)ethan-1-ol (2m): The product (88.4 mg,
99% yield) was isolated using flash chromatography (30%
EtOAc/PE), as yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.26
(d, J = 7.9 Hz, 2H), 7.11 (d, J = 7.8 Hz, 2H), 4.83 (q, J = 6.4
Hz, 1H), 2.45 (d, J = 7.2 Hz, 2H), 2.02 (br, 1H), 1.91 – 1.78
(m, 1H), 1.46 (d, J = 6.5 Hz, 3H), 0.90 (d, J = 6.6 Hz, 6H);
13C{1H} NMR (101 MHz, CDCl3) δ 143.1, 140.9, 129.2,
125.2, 70.2, 45.1, 30.2, 25.0, 22.4; HRMS (ESI-TOF) m/z:
[M+H-H2O]+ Calcd for C12H17: 161.1325; found: 161.1327.
FTIR (KBr): 3340, 1868, 1791, 1457, 1380, 1078, 798 cm-1.
Analytical data is in accordance with literature data. 16
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(2-Iodophenyl)methanol (2g): The product (108.9 mg, 93%
yield) was isolated using flash chromatography (40%
1
EtOAc/PE), as yellow solid. H NMR (400 MHz, CDCl3) δ
7.83-7.81 (m, 1H), 7.50 – 7.43 (m, 1H), 7.39-7.35 (m, 1H),
7.02 – 6.98 (m, 1H), 4.68 (s, 2H), 2.10 (br, 1H); 13C{1H}
NMR (101 MHz, CDCl3) δ 142.6, 139.2, 129.3, 128.5, 128.4,
97.4, 69.3; HRMS (ESI-TOF) m/z: [M+H-H2O]+ Calcd for
C7H6I: 216.9509; found: 216.9504. FTIR (KBr): 3049, 2961,
1457, 1435, 1326, 1195, 1035, 1011, 739 cm-1. Analytical data
is in accordance with literature data. 9, 11
Cyclopentyl(phenyl)methanol (2n): The product (67.0 mg,
76% yield) was isolated using flash chromatography (DCM),
as yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.45 – 7.26 (m,
5H), 4.40 (d, J = 8.5 Hz, 1H), 2.22 (br, J = 8.1 Hz, 1H), 1.93 –
1.85 (m, 2H), 1.72 – 1.36 (m, 7H); 13C{1H} NMR (101 MHz,
CDCl3) δ 144.5, 128.3, 127.5, 126.5, 79.1, 47.6, 29.5, 25.5;
HRMS (ESI-TOF) m/z: [M+Na]+ Calcd for C12H16NaO+:
199.1093; found: 199.1109. FTIR (KBr): 3420, 3028, 1489,
1455, 1024, 761, 700 cm-1. Analytical data is in accordance
with literature data. 17
(2-Methoxyphenyl)methanol (2h): The product (57.4 mg, 83%
yield) was isolated using flash chromatography (20%
EtOAc/PE), as yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.28
(t, J = 7.3 Hz, 2H), 6.99 – 6.84 (m, 2H), 4.69 (s, 2H), 3.87 (s,
3H), 2.38 (br, 1H); 13C{1H} NMR (101 MHz, CDCl3) δ 157.5,
129.0, 128.8, 120.7, 110.2, 62.2, 55.3; HRMS (ESI-TOF) m/z:
[M+H-H2O]+ Calcd for C8H9O: 121.0648; found: 121.0648.
FTIR (KBr): 3411, 1338,1260, 1072, 781 cm-1. Analytical data
is in accordance with literature data. 13
Diphenylmethanol (2o): The product (75.6 mg, 82% yield)
was isolated using flash chromatography (15% EtOAc/PE), as
off white solid. 1H NMR (400 MHz, CDCl3) δ 7.48 – 7.20 (m,
10H), 5.82 (s, 1H), 2.52 (br, 1H); 13C{1H} NMR (101 MHz,
CDCl3) δ 143.83, 128.51, 127.58, 126.58, 76.22; HRMS (ESI-
TOF) m/z: [M+H-H2O]+ Calcd for C13H11: 167.0855; found:
167.0850. FTIR (KBr): 3335, 1489, 1456, 1077, 774 cm-1.
Analytical data is in accordance with literature data. 16
(4-(Benzyloxy)phenyl)methanol (2i): The product (106.4 mg,
99% yield) was isolated using flash chromatography (35%
1
EtOAc/PE), as off white solid. H NMR (400 MHz, CDCl3) δ
7.53 – 7.36 (m, 4H), 7.35 (dd, J = 8.1, 5.8 Hz, 1H), 7.27 (t, J =
7.4 Hz, 2H), 7.07 – 6.91 (m, 2H), 5.07 (s, 2H), 4.58 (s, 2H),
2.19 (br, 1H); 13C{1H} NMR (101 MHz, CDCl3) δ 158.4,
137.0, 133.5, 128.7, 128.6, 128.0, 127.5, 114.9, 70.1, 64.9;
1,2-Diphenylethan-1-ol (2p): The product (83.3 mg, 84%
+
HRMS (ESI-TOF) m/z: [M+Na]+ Calcd for C14H14NaO2 :
yield) was isolated using flash chromatography (15%
237.0886; found: 237.0884. FTIR (KBr): 3335, 2944, 2829,
1608, 1558, 1456, 1395, 1285, 1274, 1149, 1110, 997, 811,
740, 696 cm-1. Analytical data is in accordance with literature
data. 14
1
EtOAc/PE), as off white solid. H NMR (600 MHz, CDCl3) δ
7.36 – 7.31 (m, 4H), 7.30 – 7.26 (m, 3H), 7.25 – 7.20 (m, 1H),
7.20 – 7.15 (m, 2H), 4.86 (dd, J = 8.5, 4.9 Hz, 1H), 3.06 – 2.94
(m, 2H), 2.06 (br, 1H); 13C{1H} NMR (101 MHz, CDCl3) δ
143.8, 138.0, 129.5, 128.5, 128.4, 127.6, 126.6, 125.9, 75.3,
46.1; HRMS (ESI-TOF) m/z: [M+Na]+ Calcd for C14H14NaO+:
m/z calc.: 221.0937; found: 221.0946. FTIR (KBr): 3489,
3028, 2917, 2849, 1622, 1495, 1454, 1191, 1081, 1028 cm-1.
Analytical data is in accordance with literature data. 18
Naphthalen-2-ylmethanol (2j): The product (67.3 mg, 85%
yield) was isolated using flash chromatography (30%
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EtOAc/PE), as yellow solid. H NMR (400 MHz, CDCl3) δ
7.95 – 7.66 (m, 4H), 7.49-7.45 (m, 3H), 4.84 (s, 2H), 1.87 (br,
1H); 13C{1H} NMR (101 MHz, CDCl3) δ 138.3, 133.4, 132.9,
128.3, 127.9, 127.7, 126.2, 125.9, 125.4, 125.2, 65.5; HRMS
(ESI-TOF) m/z: [M+H-H2O]+ Calcd for C11H9: 141.0699;
found: 141.0700. FTIR (KBr): 3421, 2967, 1507, 1436, 1362,
1328, 1247, 1034, 861, 818, 742 cm-1. Analytical data is in
accordance with literature data. 7
1-(6-Methoxynaphthalen-2-yl)ethan-1-ol (2q): The product
(100.2 mg, 99% yield) was isolated using flash
chromatography (25% EtOAc/PE), as off white solid. 1H
NMR (400 MHz, CDCl3) δ 7.88 – 7.63 (m, 3H), 7.47 - 7.45
(m, 1H), 7.17 – 7.11 (m, 2H), 5.00 (q, J = 6.5 Hz, 1H), 3.91 (s,
3H), 2.25 (br, 1H), 1.56 (d, J = 6.4 Hz, 3H); 13C{1H} NMR
(101 MHz, CDCl3) δ 157.6, 141.0, 134.0, 129.4, 128.8, 127.1,
124.4, 123.8, 118.9, 105.7, 70.4, 55.3, 25.0; HRMS (ESI-
1-Phenylethan-1-ol (2k): The product (60.6 mg, 99% yield)
was isolated using flash chromatography (25% EtOAc/PE), as
yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.42 – 7.30 (m, 4H),
7.31 – 7.24 (m, 1H),4.85 (q, J = 6.5 Hz, 1H), 2.57 (br, 1H),
1.47 (d, J = 6.5 Hz, 3H); 13C{1H} NMR (101 MHz, CDCl3) δ
145.9, 128.5, 127.4, 125.4, 70.3, 25.1; HRMS (ESI-TOF) m/z:
[M+H-H2O]+ Calcd for C8H9: 105.0699; Found: 105.0702.
FTIR (KBr): 3369, 2970, 1735, 1654, 1451, 1079 cm-1.
Analytical data is in accordance with literature data. 14
+
TOF) m/z: [M+Na]+ Calcd for C13H14NaO2 : 225.0886; Found:
225.0879. FTIR (KBr): 3355, 2961, 1918, 1868, 1697, 1456,
1074, 961, 785 cm-1. Analytical data is in accordance with
literature data. 16
tert-Butyl benzoylcarbamate (2r): The product (69.7 mg, 63%
yield) was isolated using flash chromatography (25%
1
1-(p-Tolyl)ethan-1-ol (2l): The product (65.4 mg, 96% yield)
was isolated using flash chromatography (15% EtOAc/DCM),
EtOAc/PE), as white solid. H NMR (400 MHz, CDCl3) δ
8.21 (br, 1H), 7.86 – 7.80 (m, 2H), 7.58 – 7.53 (m, 1H), 7.49 –
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