The Journal of Organic Chemistry
Article
white solid, mp 150−151 °C [149 °C],45 94% (58.7 mg). H NMR
(400 MHz, DMSO) δ 8.89−8.84 (m, 1H), 8.80 (d, J = 7.7 Hz, 1H),
8.15−8.09 (m, 1H), 8.01−7.95 (m, 1H), 7.88 (s, 1H), 7.75−7.59 (m,
4H), 5.02 (s, 2H). 13C{1H} NMR (100 MHz, CDCl3) δ 134.5, 131.4,
130.7, 130.4, 130.1, 128.7, 126.9, 126.82, 126.80, 126.6, 125.9, 124.3,
123.2, 122.5, 64.1.
MHz, CDCl3) δ 10.70 (s, 1H), 7.84 (d, J = 2.1 Hz, 1H), 7.48 (dd, J =
8.6, 2.1 Hz, 1H), 6.96 (d, J = 8.6 Hz, 1H), 4.85 (q, J = 6.4 Hz, 1H),
3.95 (s, 3H), 1.48 (d, J = 6.4 Hz, 3H). 13C{1H} NMR (101 MHz,
CDCl3) δ 170.5, 160.9, 136.6, 133.1, 126.7, 117.7, 112.0, 69.6, 52.3,
25.1.
1
1-Phenylpropan-1-ol (5i). The crude product was chromato-
graphed on silica (petroleum ether/EtOAc) to give a colorless
Benzofuran-2-ylmethanol (3r). The crude product was chromato-
graphed on silica (petroleum ether/EtOAc) to give a yellow liquid,47
83% (36.9 mg). 1H NMR (400 MHz, CDCl3) δ 7.57−7.49 (m, 1H),
7.49−7.41 (m, 1H), 7.29−7.19 (m, 2H), 6.63 (s, 1H), 4.74 (s, 2H),
2.19 (s, 1H). 13C{1H} NMR (100 MHz, CDCl3) δ 156.4, 155.1,
128.2, 124.4, 122.8, 121.1, 111.2, 104.1, 58.1.
liquid,51 91% (37.2 mg). H NMR (400 MHz, CDCl3) δ 7.38−7.31
1
(m, 4H), 7.31−7.22 (m, 1H), 4.58 (t, J = 6.6 Hz, 1H), 1.86−1.68 (m,
2H), 0.91 (t, J = 7.4 Hz, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ
144.6, 128.4, 127.5, 126.0, 76.0, 31.9, 10.1.
1-Phenylbutan-1-ol (5j). The crude product was chromatographed
on silica (petroleum ether/EtOAc) to give a colorless liquid,40 88%
(39.7 mg). 1H NMR (400 MHz, CDCl3) δ 7.36−7.32 (m, 4H), 7.30−
7.27 (m, 1H), 4.67 (dd, J = 7.5, 5.8 Hz, 1H), 1.83−1.76 (m, 2H),
1.72−1.64 (m, 1H), 1.51−1.38 (m, 1H), 1.36−1.23 (m, 1H), 0.93 (t,
J = 7.4 Hz, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ 144.9, 128.4,
127.5, 125.9, 74.4, 41.2, 19.0, 14.0.
Quinolin-2-ylmethanol (3s). The crude product was chromato-
graphed on silica (petroleum ether/EtOAc) to give a pale yellow
solid, mp 62−65 °C [63−65 °C],48 64% (30.6 mg). H NMR (400
1
MHz, CDCl3) δ 8.19 (d, J = 8.5 Hz, 1H), 8.12 (d, J = 8.5 Hz, 1H),
7.88 (d, J = 8.0 Hz, 1H), 7.78 (ddd, J = 8.4, 7.0, 1.4 Hz, 1H), 7.63−
7.56 (m, 1H), 7.34 (d, J = 8.5 Hz, 1H), 4.97 (s, 2H). 13C{1H} NMR
(100 MHz, CDCl3) δ 135.8, 128.8, 127.6, 126.7, 126.6, 125.4, 117.3,
63.1, 28.7.
1-(Naphthalen-2-yl)ethan-1-ol (5k). The crude product was
chromatographed on silica (petroleum ether/EtOAc) to give a
white solid, mp 69−70 °C [74.4 °C],49 >99% (51.4 mg). H NMR
1
1-Phenylethan-1-ol (5a). The crude product was chromato-
graphed on silica (petroleum ether/EtOAc) to give a yellow liquid,42
87% (31.9 mg). 1H NMR (400 MHz, CDCl3) δ 7.40−7.31 (m, 4H),
7.30−7.25 (m, 1H), 4.89 (q, J = 6.5 Hz, 1H), 1.49 (d, J = 6.5 Hz,
3H). 13C{1H} NMR (100 MHz, CDCl3) δ 145.8, 128.5, 127.5, 125.4,
70.4, 25.2.
1-(p-Tolyl)ethan-1-ol (5b). The crude product was chromato-
graphed on silica (petroleum ether/EtOAc) to give a colorless
liquid,40 81% (33.1 mg). 1H NMR (400 MHz, CDCl3) δ 7.26 (d, J =
7.9 Hz, 2H), 7.16 (d, J = 7.9 Hz, 2H), 4.86 (q, J = 6.4 Hz, 1H), 2.34
(s, 3H), 1.48 (d, J = 6.5 Hz, 3H). 13 C{1H} NMR (100 MHz, CDCl3)
δ 142.9, 137.2, 129.2, 125.4, 70.3, 25.1, 21.1.
(400 MHz, CDCl3) δ 7.95−7.73 (m, 4H), 7.59−7.37 (m, 3H), 5.06
(q, J = 6.1 Hz, 1H), 1.92 (s, 1H), 1.57 (d, J = 6.3 Hz, 3H). 13C{1H}
NMR (100 MHz, CDCl3) δ 143.2, 133.4, 132.9, 128.3, 127.9, 127.7,
126.1, 125.8, 123.8, 70.5, 25.1.
Di-p-tolylmethanol (5l). The crude product was chromatographed
on silica (petroleum ether/EtOAc) to give a white solid, mp 62−65
°C [69−70 °C],52 83% (52.9 mg). H NMR (400 MHz, CDCl3) δ
1
7.28−7.21 (m, 4H), 7.13 (d, J = 8.0 Hz, 4H), 5.78 (s, 1H), 2.32 (s,
6H). 13C{1H} NMR (100 MHz, CDCl3) δ 141.1, 137.1, 129.1, 129.0,
127.1, 126.4, 76.0, 21.1.
Bis(4-fluorophenyl)methanol (5m). The crude product was
chromatographed on silica (petroleum ether/EtOAc) to give a
1-(3-Methoxyphenyl)ethan-1-ol (5c). The crude product was
chromatographed on silica (petroleum ether/EtOAc) to give a
white solid, mp 43−44 °C [47−49 °C],53 71% (46.9 mg). H NMR
1
colorless liquid,42 96% (43.8 mg). H NMR (400 MHz, CDCl3) δ
1
(400 MHz, CDCl3) δ 7.37−7.27 (m, 4H), 7.08−6.95 (m, 4H), 5.80
7.31−7.20 (m, 1H), 6.94−6.92 (m, 2H), 6.82−6.79 (m, 1H), 4.85 (q,
J = 6.5 Hz, 1H), 3.80 (s, 3H), 1.47 (d, J = 6.5 Hz, 3H). 13C{1H}
NMR (100 MHz, CDCl3) δ 159.8, 147.6, 129.5, 117.7, 112.9, 110.9,
70.3, 55.2, 25.1.
(s, 1H), 2.25 (s, 1H). 13C{1H} NMR (100 MHz, CDCl3) δ 163.5
1
1
(C−F, JC−F = 246.2 Hz), 161.0 (C−F, JC−F = 246.2 Hz), 139.43
4
4
(C−F, JC−F = 2.9 Hz), 139.40 (C−F, JC−F = 2.9 Hz), 128.2 (C−F,
3JC−F = 8.1 Hz), 128.1 (C−F, JC−F = 8.1 Hz), 115.5 (C−F, JC−F
=
3
2
1-(4-Fluorophenyl)ethan-1-ol (5d). The crude product was
chromatographed on silica (petroleum ether/EtOAc) to give a yellow
21.5 Hz), 115.3 (C−F, JC−F = 21.5 Hz), 75.0. 19F NMR (377 MHz,
2
liquid,40 93% (39.1 mg). H NMR (400 MHz, CDCl3) δ 7.39−7.28
1
CDCl3) δ −114.7.
Cyclopropyl(phenyl)methanol (5n). The crude product was
chromatographed on silica (petroleum ether/EtOAc) to give a
(m, 2H), 7.09−6.97 (m, 2H), 4.87 (q, J = 6.4 Hz, 1H), 1.46 (d, J =
6.5 Hz, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ 163.3 (C−F, 1JC−F
colorless liquid,54 54% (24.0 mg). H NMR (400 MHz, CDCl3) δ
1
1
= 245.1 Hz), 160.9 (C−F, JC−F = 245.1 Hz), 141.5, 127.1 (C−F,
3
2
3JC−F = 8.1 Hz), 127.0 (C−F, JC−F = 8.1 Hz), 115.4 (C−F, JC−F
=
7.44−7.38 (m, 2H), 7.38−7.31 (m, 2H), 7.31−7.23 (m, 1H), 3.99 (d,
J = 8.2 Hz, 1H), 2.12 (s, 1H), 1.25−1.16 (m, 1H), 0.67−0.58 (m,
1H), 0.58−0.50 (m, 1H), 0.49−0.43 (m, 1H), 0.39−0.33 (m, 1H).
13C{1H} NMR (100 MHz, CDCl3) δ 143.8, 128.4, 127.5, 126.0, 78.5,
19.2, 3.6, 2.8.
2
21.4 Hz), 115.1 (C−F, JC−F = 21.4 Hz), 69.8, 25.3. 19F NMR (377
MHz, CDCl3) δ −115.3.
1-(4-Chlorophenyl)ethan-1-ol (5e). The crude product was
chromatographed on silica (petroleum ether/EtOAc) to give a
colorless liquid,40 97% (45.6 mg). H NMR (400 MHz, CDCl3) δ
1
Cyclohexyl(phenyl)methanol (5o). The crude product was
chromatographed on silica (petroleum ether/EtOAc) to give a
7.31 (s, 4H), 4.88 (q, J = 6.4 Hz, 1H), 1.47 (d, J = 6.4 Hz, 3H).
13C{1H} NMR (100 MHz, CDCl3) δ 144.2, 133.1, 128.6, 126.8, 69.8,
25.3.
colorless liquid,55 75% (42.8 mg). H NMR (400 MHz, CDCl3) δ
1
7.43−7.31 (m, 5H), 4.41 (d, J = 7.1 Hz, 1H), 2.03 (d, J = 12.8 Hz,
1H), 1.91 (s, 1H), 1.86−1.77 (m, 1H), 1.75−1.68 (m, 2H), 1.43−
1.40 (m, 1H), 1.30−0.95 (m, 5H). 13C{1H} NMR (100 MHz,
CDCl3) δ 143.6, 128.2, 127.4, 126.6, 79.4, 45.0, 29.3, 28.8, 26.4, 26.1,
26.0.
1-(4-Bromophenyl)ethan-1-ol (5f). The crude product was
chromatographed on silica (petroleum ether/EtOAc) to give a yellow
liquid,40 94% (56.7 mg). H NMR (400 MHz, CDCl3) δ 7.49−7.43
1
(m, 2H), 7.23 (d, J = 8.3 Hz, 2H), 4.84 (q, J = 6.4 Hz, 1H), 1.45 (d, J
= 6.5 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 144.8, 131.5, 127.2,
121.1, 69.8, 25.2.
1,1,2,2-Tetraphenylethane-1,2-diol (7a). The crude product was
chromatographed on silica (petroleum ether/EtOAc) to give a white
solid, mp 185−186 °C [185−186 °C],56 92% (101.1 mg). H NMR
1
1-([1,1′-Biphenyl]-4-yl)ethan-1-ol (5g). The crude product was
(400 MHz, CDCl3) δ 7.34−7.26 (m, 8H), 7.22−7.13 (m, 12H), 3.00
(s, 2H). 13C{1H} NMR (100 MHz, CDCl3) δ 144.1, 128.6, 127.3,
127.0, 83.0.
chromatographed on silica (petroleum ether/EtOAc) to give a white
solid, mp 95−96 °C [90−92 °C],49 99% (58.9 mg). H NMR (400
1
MHz, CDCl3) δ 7.59 (d, J = 8.1 Hz, 4H), 7.46−7.42 (m, 4H), 7.39−
7.31 (m, 1H), 4.95 (q, J = 6.5 Hz, 1H), 1.54 (d, J = 6.5 Hz, 3H).
13C{1H} NMR (100 MHz, CDCl3) δ 144.8, 140.9, 140.5, 128.8,
127.3, 127.1, 125.9, 70.2, 25.2.
1,1,2,2-Tetra-p-tolylethane-1,2-diol (7b). The crude product was
chromatographed on silica (petroleum ether/EtOAc) to give a white
solid, mp 174−176 °C [183−184 °C],57 >99% (126.3 mg). 1H NMR
(400 MHz, CDCl3) δ 7.15 (d, J = 8.2 Hz, 8H), 6.96 (d, J = 8.1 Hz,
8H), 2.95 (s, 2H), 2.27 (s, 12H). 13C{1H} NMR (100 MHz, CDCl3)
δ 141.5, 136.3, 128.5, 127.9, 82.8, 20.9.
Methyl 2-Hydroxy-5-(1-hydroxyethyl)benzoate (5h). The crude
product was chromatographed on silica (petroleum ether/EtOAc) to
give a white solid,50 mp 52−54 °C, >99% (58.4 mg). H NMR (400
1
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J. Org. Chem. 2021, 86, 2474−2488