The Journal of Organic Chemistry
Article
(4-Bromophenyl)methanol (2e).25 White solid; yield: 335 mg,
90%; gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; 1H NMR
(600 MHz, DMSO-d6) δ: 7.51 (d, J = 8.4 Hz, 2H), 7.27 (d, J = 8.4
Hz, 2H), 5.26 (t, J = 5.7 Hz, 1H), 4.46 (d, J = 5.6 Hz, 2H); 13C{1H}
NMR (151 MHz, DMSO-d6) δ: 142.5, 131.4, 129.0, 120.0, 62.6.
(4-Iodophenyl)methanol (2f).25 White solid; yield: 421 mg, 90%;
gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; 1H NMR (600
MHz, DMSO-d6) δ: 7.61 (d, J = 8.2 Hz, 2H), 7.06 (d, J = 8.2 Hz,
2H), 5.17 (t, J = 5.7 Hz, 1H), 4.38 (d, J = 5.7 Hz, 2H); 13C{1H}
NMR (151 MHz, DMSO-d6) δ: 142.9, 137.2, 129.2, 92.7, 62.7.
2-Methylbenzyl Alcohol (2g).29 Colorless liquid; yield: 220 mg,
90%; gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; 1H NMR
(600 MHz, CDCl3) δ: 7.38−7.32 (m, 1H), 7.25−7.20 (m, 2H),
7.20−7.16 (m, 1H), 4.67 (s, 2H), 2.35 (s, 3H), 2.07 (br, s, 1H);
13C{1H} NMR (151 MHz, CDCl3) δ: 138.8, 136.2, 130.4127.9,
127.6, 126.1, 63.5, 18.7.
13C{1H} NMR (101 MHz, DMSO-d6) δ: 156.6, 133.2, 128.5, 115.2,
63.2.
4-Cyanobenzyl alcohol (2r).33 Colorless liquid; yield: 239 mg,
90%; gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; 1H NMR
(600 MHz, DMSO-d6) δ: 7.79 (d, J = 7.9 Hz, 2H), 7.51 (d, J = 8.4
Hz, 2H), 5.46 (t, J = 5.7 Hz, 1H), 4.59 (d, J = 5.5 Hz, 2H); 13C{1H}
NMR (151 MHz, DMSO-d6) δ: 149.0, 132.5, 127.4, 119.5, 109.8,
62.7.
4-Nitrobenzyl Alcohol (2s).34 White solid; yield: 275 mg, 90%;
1
gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; H NMR (600
MHz, DMSO-d6) δ: 8.20 (d, J = 8.7 Hz, 1 H), 7.59 (d, J = 8.5 Hz,
1H), 5.53 (s, 1H), 4.64 (s, 1H); 13C{1H} NMR (151 MHz, DMSO-
d6) δ: 151.3, 127.5, 123.8, 62.5.
1,4-Benzenedimethanol (2t).35 White solid; yield: 248 mg, 90%;
1
gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; H NMR (600
MHz, DMSO-d6) δ: 7.25 (s, 4H), 5.12 (t, J = 5.7 Hz, 2H), 4.47 (d, J
= 5.7 Hz, 4H); 13C{1H} NMR (151 MHz, DMSO-d6) δ: 141.3,
126.7, 63.2.
2-Methoxybenzyl Alcohol (2h).30 Colorless liquid; yield: 207 mg,
75%; gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; 1H NMR
(400 MHz, CDCl3) δ: 7.16 (t, J = 7.9 Hz, 2H), 6.83 (t, J = 7.4 Hz,
1H), 6.76 (d, J = 8.3 Hz, 1H), 4.56 (s, 2H), 3.72 (s, 3H), 2.58 (s,
1H). 13C{1H} NMR (101 MHz, CDCl3) δ: 157.4, 129.2, 128.9,
128.7, 120.7, 110.2, 61.8, 55.3.
1-Naphthalenemethanol (2u).27 White solid, yield: 275 mg, 87%
1H NMR (600 MHz, DMSO-d6) δ: 8.10 (d, J = 7.8 Hz, 1H), 7.94 (d,
J = 7.6 Hz, 1H), 7.83 (d, J = 8.2 Hz, 1H), 7.54−7.48 (m, 4H), 5.31 (s,
1H), 4.99 (s, 2H); 13C{1H} NMR (151 MHz, DMSO-d6) δ: 138.3,
133.6, 131.2, 128.8, 127.7, 126.3, 126.1, 125.9, 124.7, 124.2, 61.6.
1,4-Benzenedimethanol (2v).35 White solid; yield: 248 mg, 90%;
2-Hydroxybenzyl Alcohol (2i).31 White solid; yield: 174 mg, 70%;
1
gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; H NMR (600
1
MHz, CDCl3) δ: 7.21 (t, J = 7.7 Hz, 1H), 7.03 (d, J = 7.4 Hz, 1H),
6.92−6.82 (m, 2H), 4.86 (s, 2H), 2.28 (s, 1H); 13C{1H} NMR (151
MHz, CDCl3) δ: 156.1, 129.6, 127.9, 124.6, 120.1, 116.6, 64.7.
2-Nitrobenzyl Alcohol (2j).27 White solid; yield: 282 mg, 92%;
gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; 1H NMR (600
MHz, CDCl3) δ: 8.09 (d, J = 8.2 Hz, 1H), 7.74 (d, J = 7.7 Hz, 1H),
7.67 (dd, J = 10.8, 4.3 Hz, 1H), 7.47 (dd, J = 11.3, 4.2 Hz, 1H), 4.97
(s, 2H), 2.72 (s, 1H); 13C{1H} NMR (151 MHz, CDCl3) δ: 146.6,
135.8, 133.1, 128.9, 127.5, 124.0, 61.5.
gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; H NMR (600
MHz, DMSO-d6) δ: 7.25 (s, 4H), 5.12 (t, J = 5.7 Hz, 2H), 4.47 (d, J
= 5.7 Hz, 4H); 13C{1H} NMR (151 MHz, DMSO-d6) δ: 141.3,
126.7, 63.2.
3-Phenylpropan-1-ol (2w).25 Colorless liquid; yield: 245 mg, 90%;
1
gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; H NMR (600
MHz, DMSO-d6) δ: 7.27 (t, J = 7.6 Hz, 2H), 7.23−7.12 (m, 3H),
4.46 (s, 1H), 3.43−3.41 (m, 2H), 2.61 (t, J = 7.7 Hz, 2H), 1.74−1.69
(m, 2H); 13C{1H} NMR (151 MHz, DMSO-d6) δ: 142.7, 128.7 (d, J
= 9.1 Hz), 126.1, 60.6, 34.8, 32.1.
3-Methylbenzyl Alcohol (2k).32 Colorless liquid; yield: 212 mg,
87%; gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; 1H NMR
(600 MHz, CDCl3) δ: 7.26 (t, J = 7.5 Hz, 1H), 7.19 (s, 1H), 7.16 (d,
J = 7.5 Hz, 1H), 7.12 (d, J = 7.5 Hz, 1H), 4.65 (s, 2H), 2.56 (br, s,
1H), 2.37 (s, 3H); 13C{1H} NMR (151 MHz, CDCl3) δ: 140.9,
138.3, 128.6, 128.5, 127.9, 124.2, 65.4, 21.5.
1-Phenylbutane-1,4-diol (2x).36 Colorless liquid; yield: 239 mg,
72%; gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; 1H NMR
(600 MHz, DMSO-d6) δ: 7.81−6.64 (m, 5H), 5.12 (d, J = 3.8 Hz,
1H), 4.51 (d, J = 5.3 Hz, 1H), 4.36 (t, J = 4.6 Hz, 1H), 3.37 (dd, J =
11.2, 5.6 Hz, 2H), 1.66−1.55 (m, 2H), 1.54−1.28 (m, 2H); 13C{1H}
NMR (151 MHz, DMSO-d6) δ: 146.9, 128.4, 127.0, 126.3, 72.7, 61.3,
36.4, 29.5.
3-Methoxybenzyl Alcohol (2l).32 Colorless liquid; yield: 215 mg,
78%; gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; 1H NMR
(400 MHz, CDCl3) δ: 7.17 (t, J = 8.1 Hz, 1H), 6.83 (d, J = 7.6 Hz,
2H), 6.73 (d, J = 11.2 Hz, 1H), 4.54 (s, 2H), 3.71 (s, 3H), 2.26 (br, s,
1H); 13C{1H} NMR (101 MHz, CDCl3) δ: 159.8, 142.7, 129.6,
119.1, 113.2, 112.3, 64.9, 55.0.
Butane-1,4-diol (2y).37 Yield: colorless liquid; 144 mg, 80%;
1
gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; H NMR (600
MHz, CDCl3) δ: 3.62 (t, J = 5.8 Hz, 4H), 2.28 (s, 2H), 1.64−1.61
(m, 4H); 13C{1H} NMR (151 MHz, CDCl3) δ: 62.6, 29.8.
Decane-1,10-diol (2z).38 White solid; yield: 341 mg, 98%; gradient
3-Nitrobenzyl Alcohol (2m).27 White solid; yield: 214 mg, 70%;
gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; 1H NMR (400
MHz, CDCl3) δ: 8.13 (d, J = 9.3 Hz, 1H), 8.03 (t, J = 8.8 Hz, 1H),
7.61 (t, J = 7.1 Hz, 1H), 7.45 (q, J = 8.2 Hz, 1H), 4.72 (s, 2H), 3.54
(br, s, 1H); 13C{1H} NMR (101 MHz, CDCl3) δ: 148.2, 143.0,
132.8, 129.4, 122.3, 121.3, 63.6.
1
eluent: EtOAc/petroleum ether: 1/4 to 1/2; H NMR (400 MHz,
CDCl3) δ: 3.64 (t, J = 6.6 Hz, 4H), 1.68−1.50 (m, 4H), 1.42 (br, s,
2H), 1.30 (br, s, 12H); 13C{1H} NMR (101 MHz, CDCl3) δ: 63.1,
32.8, 29.5,29.4, 25.7.
4-Tolylmethanol (2n).28 Yield: white solid; 220 mg, 90%; gradient
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge at
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1
eluent: EtOAc/petroleum ether: 1/4 to 1/2; H NMR (600 MHz,
sı
DMSO-d6) δ: 7.19 (d, J = 7.8 Hz, 2H), 7.12 (d, J = 7.8 Hz, 2H), 5.09
(t, J = 5.7 Hz, 1H), 4.44 (d, J = 5.7 Hz, 2H), 2.28 (s, 3H); 13C{1H}
NMR (151 MHz, DMSO-d6) δ: 134.0, 136.0, 129.1, 127.0, 63.2, 21.2.
4-tert-Butylbenzyl Alcohol (2o).28 Colorless liquid; yield: 262 mg,
80%; gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; 1H NMR
(600 MHz, DMSO-d6) δ: 7.11 (d, J = 8.3 Hz, 2H), 6.99 (d, J = 8.4
Hz, 2H), 4.30 (s, 2H), 1.06 (s, 9H); 13C{1H} NMR (151 MHz,
DMSO-d6) δ: 149.5, 140.0, 126.8, 125.2, 63.2, 34.6, 31.7.
Details for experiments, characterizations, and compu-
AUTHOR INFORMATION
Corresponding Authors
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4-Methoxybenzyl Alcohol (2p).27 Colorless liquid; yield: 215 mg,
78%; gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; 1H NMR
(600 MHz, DMSO-d6) δ: 7.10 (d, J = 8.4 Hz, 2H), 6.73 (d, J = 8.5
Hz, 2H), 4.38 (s, 2H), 3.64 (s, 3H); 13C{1H} NMR (151 MHz,
DMSO-d6) δ: 158.7, 135.0, 128.4, 113.9, 63.1, 55.4.
Yan-Na Ma − School of Chemistry and Chemical Engineering,
Henan Key Laboratory of Boron Chemistry and Advanced
Energy Materials, Henan Normal University, Xinxiang
453007, China; Green Catalysis Center and College of
Chemistry, Zhengzhou University, Zhengzhou 450001,
4-Hydroxybenzyl Alcohol (2q).31 White solid; yield: 174 mg, 70%;
gradient eluent: EtOAc/petroleum ether: 1/4 to 1/2; 1H NMR (400
MHz, DMSO-d6) δ: 9.22 (s, 1H), 7.10 (d, J = 8.1 Hz, 2H), 6.70 (d, J
= 8.0 Hz, 2H), 4.94 (t, J = 5.2 Hz, 1H), 4.36 (d, J = 4.9 Hz, 2H);
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J. Org. Chem. 2021, 86, 5305−5316