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JOURNAL OF CHEMICAL RESEARCH 2009
7
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ensuing mixture was extracted with ethyl acetate. The organic phase
was dried over anhydrous MgSO4. After removal of the solvent,
2-methylcyclohexanol (2a) (1.09 g, 95.2%) was obtained as a
colourless oil (Table, run 1).
2,3,5-Trimethylcyclohexanol (2u):5 GH (400 MHz, CDCl3) 0.78–1.72
(16H, m), 2.00 (1H, s, OH), 3.40–3.60 (1H, m, CHOH). The isomeric
ratio was not determined due to the complexity of the NMR spectrum.
4-Hydroxybenzylamine (1y):35 Colourless solid, m.p. 117°C; GH
(270 MHz, CD3OD) 3.70 (2H, s), 6.74 (2H, m), 7.16 (2H, m); GC (67.8
MHz, CDCl3) 46.4 (CH2), 116.8 (2C, CH), 130.0 (2C, CH), 134.2
(Cquat), 158.2 (Cquat).
2-Methylcyclohexanol (2a, a mixture of syn and anti-isomers):22
Qmax (neat/cm-1) 3370 (bs, OH), 2920, 2880, 1450, 1062, 1045, 1030,
978, 917, 840; GH (400 MHz, CDCl3) 1.02–1.88 (12H, m), 2.02 (1H,
s, OH), 3.14 (0.82 H, dt, J = 4.2 and 9.4 Hz, CHOH, anti-isomer),
3.80 (0.18 H, quintet, J = 2.6 Hz, CHOH, syn-isomer); GC (67.8 MHz,
CDCl3) for syn-isomer: 20.6, 24.5, 28.8, 30.9, 32.5, 35.8, 71.1; for
anti-isomer: 18.5, 25.2, 25.7, 33.6, 35.5, 40.2, 76.5; MS (EI, 70 eV)
m/z (%) 114 (M+) (38), 96 (100), 81 (88), 68 (64), 58 (58).
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by column chromatography on silica gel, when mixtures
of structures were obtained from the reactions. All of the
compounds were compared with authentic samples and/or
their structures were assigned on the basis of 1H NMR, IR and
GC-MS spectroscopic data.
3-Methylcyclohexanol (2b, a mixture of syn and anti-isomers):22
Qmax (neat/cm-1) 3380 (bs, OH), 2940, 2880, 1452, 1105, 1045, 1030,
1000, 945, 935; GH (400 MHz, CDCl3) 0.98–1.80 (12H, m), 2.00
(1H, s, OH), 3.24 (0.78H, m, CHOH, anti-isomer), 3.72 (0.22H, m,
CHOH, syn-isomer); GC (67.8 MHz, CDCl3) for syn-isomer: 20.0,
22.0, 26.5, 33.1, 34.2, 41.5, 66.9; for anti-isomer: 22.3, 24.2, 31.4,
34.1, 35.4, 44.7, 70.8; MS (EI, 70 eV) m/z (%) 114 (M+) (3.7), 96
(100), 81 (62), 71 (62).
Received 26 September 2008; accepted 10 November 2008
Paper 08/0188 doi: 10.3184/030823409X393637
Published online: 16 January 2009
4-Methylcyclohexanol (2c, a mixture of syn and anti-isomers):22
Qmax (neat/cm-1) 3370 (bs, OH), 2920, 1450, 1358, 1185, 1047, 980; GH
(400 MHz, CDCl3) 0.86–1.78 (12H, m), 2.00 (1H, s, OH), 3.40 (0.79H,
m, CHOH, anti-isomer), 3.80–3.84 (0.21H, m, CHOH, syn-isomer);
GC (67.8 MHz, CDCl3) for syn-isomer: 21.6, 29.0 (2C), 31.1, 32.2 (2C),
66.9; for anti-isomer: 21.6, 31.4 33.0 (2C), 35.3 (2C), 70.6; MS (EI, 70
eV) m/z (%) 114 (M+) (5.5), 96 (100), 81 (95), 70 (38), 57 (55).
4-Ethylcyclohexanol (2g, a mixture of syn and anti-isomers):5
Qmax (neat/cm-1) 3380 (bs, OH), 2925, 2865, 1450, 1083, 1052; GH
(400 MHz, CDCl3) 0.83–1.74 (14H, m), 2.02 (1H, s, OH), 3.44 (0.81H,
m, CHOH, anti-isomer), 3.74–3.80 (0.19H, m, CHOH, syn-isomer).
2-n-Propylcyclohexanol (2h, a mixture of syn and anti-isomers):5
GH (400 MHz, CDCl3) 0.90–1.78 (16H, m), 2.00 (1H, s, OH), 3.10
(0.83H, dt, J = 4.0 and 9.2 Hz, CHOH, anti-isomer), 3.68 (0.17H,
quintet, J = 2.4 Hz, CHOH, syn-isomer).
References
1
2
3
D.J. Sikkema, P. Hoogland, J. Bik and P.T. Lam, Polymer, 1986, 27,
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4-i-Propylcyclohexanol (2i, a mixture of syn and anti-isomers):5 GH
(400 MHz, CDCl3) 0.86–1.72 (16H, m), 1.98 (1H, s, OH), 3.40 (0.88H,
m, CHOH, anti-isomer), 3.70–3.76 (0.12H, m, CHOH, syn-isomer).
4-n-Butylcyclohexanol (2j, anti-isomer):29-31 GH (400 MHz, CDCl3)
0.86–1.72 (18H, m), 1.96 (1H, s, OH), 3.42 (0.95H, m, CHOH, anti-
10 F. Sabra, J. Bassus and R. Lamartine, Mol. Cryst Liq. Cryst., 1990,
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11 L.W. Covert, R. Connor and H. Adkins, J. Am. Chem. Soc., 1932, 54, 1651.
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isomer), 3.68–3.70 (0.05H, m, CHOH, syn-isomer).
29-31
4-t-Butylcyclohexanol (2k, anti-isomer):
Q
max
(neat/cm-1) 3345,
2985, 2880, 1452, 1370, 1068; GH (400 MHz, CDCl3) 0.90–0.96 (2H,
m), 1.02 (9H, s, But), 1.20–1.22 (2H, m), 1.60–1.82 (5H, m), 2.02
(1H, s, OH), 3.44 (1H, m, CHOH).
30
2-t-Butylcyclohexanol (2l, anti-isomer):
Q
max
(neat/cm-1) 3490 (bs,
OH), 2935, 1477, 1450, 1385, 1371, 1205, 973; GH (400 MHz, CDCl3)
0.88–0.92 (2H, m), 1.00 (9H, s, But), 1.18–1.21 (2H, m), 1.64–1.80
(5H, m), 2.00 (1H, s, OH), 3.14 (1H, dt, J = 4.0 and 9.4 Hz, CHOH).
3-t-Butylcyclohexanol (2m, anti-isomer):31 GH (400 MHz, CDCl3)
0.86–0.90 (2H, m), 1.00 (9H, s, But), 1.16–1.20 (2H, m), 1.62–1.80
(5H, m), 2.00 (1H, s, OH), 3.22 (1H, m, CHOH).
4-t-Pentylcyclohexanol (2n, anti-isomer):33 GH (400 MHz, CDCl3)
0.70–0.76 (3H, t, J = 9.8 Hz), 0.80–0.84(4H, m), 0.88 (6H, s), 1.22–1.34
(3H, m), 1.50–1.80 (4H, m), 2.00 (1H, s, OH), 3.50 (1H, m, CHOH).
2,3-Dimethylcyclohexanol (2o):34 Qmax (neat/cm-1) 3375 (bs, OH),
2925, 1450, 1101, 1050, 1015; GH (400 MHz, CDCl3) 0.83–1.74 (14H,
m), 2.00 (1H, s, OH), 3.42–3.68 (1H, m, CHOH). The isomeric ratio
was not determined due to the complexity of the NMR spectrum.
3,4-Dimethylcyclohexanol (2p):5 Qmax (neat/cm-1) 3380 (bs, OH),
2920, 2870, 1452, 1365, 1102, 1037; GH (400 MHz, CDCl3) 0.80–1.72
(14H, m), 2.02 (1H, s, OH), 3.40–3.64 (1H, m, CHOH). The isomeric
ratio was not determined due to the complexity of the NMR spectrum.
3,5-Dimethylcyclohexanol (2q):5 Qmax (neat/cm-1) 3370 (bs, OH),
2910, 1455, 1345, 1027, 900, 848; GH (400 MHz, CDCl3) 0.84–1.78
(14H, m), 1.98 (1H, s, OH), 3.44–3.68 (1H, m, CHOH). The isomeric
ratio was not determined due to the complexity of the NMR spectrum.
2,5-Dimethylcyclohexanol (2r):5 Qmax (neat/cm-1) 3385 (bs, OH),
2915, 1453, 1129; GH (400 MHz, CDCl3) 0.82–1.74 (14H, m), 2.00
(1H, s, OH), 3.40–3.62 (1H, m, CHOH). The isomeric ratio was not
determined due to the complexity of the NMR spectrum.
4-Methyl-2-t-butylcyclohexanol (2s):5 GH (400 MHz, CDCl3) 0.78–1.70
(18H, m), 1.98 (1H, s, OH), 3.36–3.58 (1H, m, CHOH). The isomeric ratio
was not determined due to the complexity of the NMR spectrum.
2,4,6-Trimethylcyclohexanol (2t):5 GH (400 MHz, CDCl3) 0.82–1.70
(16H, m), 2.00 (1H, s, OH), 3.44–3.62 (1H, m, CHOH). The isomeric
ratio was not determined due to the complexity of the NMR spectrum.