The Journal of Organic Chemistry
Page 6 of 10
o
MHz, CDCl
3
, 24 C, d): 7.19 (d, J = 8.7 Hz, 2H), 6.77 (d, J =
3,5-Dimethoxyphenol, 6u
1
3
1
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
3
3
4
4
4
4
4
4
4
4
4
4
5
5
5
5
5
5
5
5
5
5
6
8
.7 Hz, 2H), 5.06 (s, 1H); C{ H} NMR (100 MHz, CDCl ,
3
+
Using the general procedure, the crude mixture was purified
by column chromatography (EtOAc:hexanes = 1:10) to give
o
24 C, d): 154.3, 129.6, 125.6, 116.8; HRMS (EI) m/z: [M]
Calcd. for C ClO 128.0029; Found 128.0032; FTIR (neat,
cm ) 3351, 2928, 1590, 1495, 1433, 1369, 1240, 1095, 822.
H
5
1
6
the product 6u (32 mg, 41% yield) as a white solid. NMR
-1
o
(
(
400 MHz, CDCl
3
, 24 C, d): 6.07 (s, 1H), 6.02 (s, 2H), 3.76
1
3
1
o
3
s, 6H); C{ H} NMR (100 MHz, CDCl , 24 C, d): 161.7,
4
-Bromophenol, 6p
+
157.5, 94.4, 93.2, 55.4; HRMS (EI) m/z: [M] Calcd. for
C H O 154.0630, found 154.0631; FTIR (neat, cm ) 3441,
8 10 3
2924, 2851, 1605, 1460, 1206, 1160, 1063, 823, 679 cm
-1
Using the general procedure, the crude mixture was purified
by column chromatography (EtOAc:hexanes = 1:10) to give
the product 6p (41 mg, 47% yield) as a white solid. H NMR
-1
1
o
(
400 MHz, CDCl
3
, 24 C, d): 7.35-7.31 (m, 2H), 6.74-6.70 (m,
2,4-Dichlorophenol, 6v
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
3
1
o
2
1
C
H); C{ H} NMR (100 MHz, CDCl
32.6, 117.3, 112.9; HRMS (EI) m/z: [M] Calcd. for
BrO 171.9524, found 171.9528; FTIR (neat, cm ) 3389,
587, 1495, 1432, 1236, 1069, 1007, 821 cm .
3
, 24 C, d): 154.8,
Using the general procedure, the crude mixture was purified
by column chromatography (EtOAc:hexanes = 1:9) to give the
+
-1
H
5
1
6
product 6v (59 mg, 73% yield) as a white solid. H NMR (400
-1
1
o
MHz, CDCl
3
, 24 C, d): 7.33 (d, J = 2.5 Hz 1H), 7.15 (dd, J =
8
.7, 2.4 Hz, 1H), 7.95 (d, J = 16.7 Hz, 1H), 5.56 (s, 1H);
4
-Iodophenol, 6q
13
1
o
C{ H} NMR (100 MHz, CDCl
3
, 24 C, d): 150.3, 128.7,
+
Using the general procedure, the crude mixture was purified
by column chromatography (EtOAc:hexanes = 1:9) to give the
product 6q (108 mg, 98% yield) as an orange solid. H NMR
(400 MHz, CDCl
= 8.6 Hz, 2H); C{ H} NMR (100 MHz, CDCl , 24 C, d):
3
155.2, 138.6, 117.9, 83.0; HRMS (EI) m/z: [M] Calcd. for
128.6, 125.7, 120.5, 117.2; HRMS (EI) m/z: [M] Calcd. for
C H Cl O 161.9639, found 161.9641; FTIR (neat, cm )
6 4c 2
3533, 2929, 2853, 2362, 2356, 1650, 1585, 1480, 1410, 1282,
1188, 865, 812, 723.
-1
1
o
3
3
, 24 C, d): 7.52(d, J = 8.7 Hz, 2H), 6.63(d, J
1
1
o
+
1-Naphthol, 6w
-
1
C
2
7
H
8
O
2
124.0524, found 124.0525; FTIR (neat, cm ) 3386,
Using the general procedure, the crude mixture was purified
by column chromatography (EtOAc:hexanes = 1:8) to give the
product 6w (59 mg, 79% yield) as an orange solid. H NMR
910, 1590, 1496, 1473, 1254, 1206, 830.
1
3-Chlorophenol, 6r
(400 MHz, CDCl
3
, 21 °C, δ): 8.23-8.15 (m, 1H), 7.86-7.79 (m,
Using the general procedure, the crude mixture was purified
by column chromatography (ether:pentane = 1:9) to give the
product 6r (28 mg, 43% yield) as a yellow oil. H NMR (400
MHz, CDCl
H), 6.86 (s, 1H), 6.72 (d, J = 8.0 Hz, 1H); C{ H} NMR
100 MHz, CDCl
16.0, 113.9; HRMS (EI) m/z: [M] Calcd. for C
28.0023, found 128.0029; FTIR (neat, cm ) 3376, 2927,
1H), 7.54-7.47 (m, 2H), 7.45 (d, J = 8.3 Hz, 1H), 7.31 (t, J =
1
3
1
7.8 Hz, 1H), 6.82 (d, J = 7.4 Hz, 1H), 5.38 (br s, 1H); C{ H}
NMR (100 MHz, CDCl , 22 °C, δ): 151.5, 134.9, 127.8,
126.6, 126.0, 125.4, 124.5, 121.7, 120.8, 108.7; HRMS (EI)
m/z: [M] Calcd. for C10
FTIR (neat, cm ) 3257, 3052, 2926, 1699, 1674, 1633, 1598,
1
3
o
3
, 24 C, d): 7.15 (t, J = 8.1 Hz, 1H), 6.92-6.89 (m,
1
3
1
+
1
(
1
1
2
H
8
O 144.0575, found 144.0573;
-1
o
3
, 24 C, d): 156.4, 135.0, 130.6, 121.1,
+
1518, 1457, 1386, 1269, 1082, 1043, 1014, 875, 790, 766.
6
H
5
ClO
-1
2-Naphthol, 6x
852, 1590, 1475, 1444, 1246, 999, 886, 771, 677.
Using the general procedure, the crude mixture was purified
2-Chlorophenol, 6s
by column chromatography (EtOAc:hexanes = 1:8) to give the
product 6x (65 mg, 90% yield) as a white solid. H NMR (400
1
Using the general procedure, the crude mixture was purified
by column chromatography (ether:pentane = 1:9) to give the
product 6s (13 mg, 20% yield) as a yellow oil. H NMR (400
MHz, CDCl
.6 Hz, 1H), 7.00 (d, J = 8.0 Hz, 1H), 6.88 (t, J = 15.6 Hz, 1H)
.60 (s, 1H); C{ H} NMR (100 MHz, CDCl
51.7, 129.2, 128.4, 121.3, 120.1, 116.4; HRMS (EI) m/z:
MHz, CDCl
.2 Hz, 1H), 7.44 (t, J = 7.5, 1H), 7.34 (t, J = 7.5 Hz, 1H), 7.16
(d, J = 2.0 Hz, 1H), 7.12 (dd, J = 8.8, 2.5 Hz, 1H), 5.40 (br s,
3
, 21 °C, δ): 7.77 (t, J = 8.2 Hz, 2H), 7.68 (d, J =
1
8
o
3
, 24 C, d): 7.31 (d, J = 8.0 Hz, 1H), 7.54 (t, J =
1
3
1
1H); C{ H} NMR (100 MHz, CDCl
3
, 21 °C, δ): 153.5,
7
5
1
[
(
1
3
1
o
134.7, 130.0, 129.0, 127.9, 126.7, 126.5, 123.7, 117.9, 109.6;
HRMS (EI) m/z: [M] Calcd. for C10H O 144.0575, found
8
144.0576; FTIR (neat, cm ) 3231, 3050, 2922, 2851, 1630,
1601, 1512, 1467, 1407, 1277, 1216, 959, 844, 814, 741.
3
, 24 C, d):
+
-1
+
M] Calcd. for C
6
H
5
ClO 128.0030, found 128.0029; FTIR
neat, cm ) 3351, 2928, 2854, 1596, 1460, 1751, 1300, 1246,
035, 845.
-1
1
2-Methoxy-6-naphthol, 6y
2,4-Dimethoxyphenol, 6t
Using the general procedure, the crude mixture was purified
by column chromatography (EtOAc:hexanes = 1:8) to give the
product 6y (64 mg, 74% yield) as a white solid. H NMR (400
MHz, CDCl , 24 C, d): 7.65 (d, J = 11.6 Hz, 1H), 7.58 (d, J =
11.6 Hz, 1H), 7.14-7.05 (m, 4H), 3.90 (s, 1H); C{ H} NMR
Using the general procedure, the crude mixture was purified
by column chromatography (EtOAc:hexanes = 1:10) to give
the product 6t (43 mg, 56% yield) as a white solid. H NMR
400 MHz, CDCl
1
o
1
3
1
3
1
o
(
3
, 24 C, d): 6.83 (d, J = 8.8 Hz, 1H), 6.49 (d,
o
(100 MHz, CDCl
3
, 24 C, d): 156.2, 151.9, 129.9, 129.8,
J = 2.4 Hz, 1H), 6.39 (dd, J = 8.8, 2.4 Hz, 1H), 5.23 (s, 1H),
1
3
1
128.6, 127.9, 119.4, 118.2, 109.8, 106.1, 55.4; HRMS (EI)
m/z: [ [M] Calcd. for C11H O 174.0681, found 174.0686;
10 2
FTIR (neat, cm ) 3307, 2922, 2849, 1624, 1487, 1382, 1379,
1217, 1031, 920, 859, 825, 691.
3
3.86 (s, 3H), 3.76 (s, 3H); C{ H} NMR (100 MHz, CDCl ,
+
o
24 C, d): 153.5, 147.1, 139.8, 114.2, 104,2, 99.5, 55.9, 55.8;
-1
+
8 10 3
HRMS (EI) m/z: [M] Calcd. for C H O 124.0524, found
24.0524; FTIR (neat, cm ) 3410, 2927, 2851, 1611, 1487,
478, 1288, 1274, 1189, 1158, 947, 856.
-1
1
1
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