Journal of the Iranian Chemical Society
instrument. The final product is then analysed by NMR
and GC-MS to confirm the products.
1.065–1.094 (m, 11H), 3.11 (s, 3H), 3.343–3.437 (d,
1
3
J = 3.76 Hz, 2H); C NMR (100 MHz, CDCl ) δ 16.59,
3
C
2
1.15, 24.90, 24.94, 33.64, 35.72, 40.07, 49.04, 68.12.
+
Characterization of hydrogenation products
GCMS; M : Mol. Formula C H O :, calculated: 174.00,
1
0
22
2
found: 174.00.
Benzyl alcohol, 11a Colourless liquid, yield: 85%.GC
1
purity: 99.73%, H NMR(400 MHz, CDCl ) δ 7.21–7.31
1-Butanol, 11h Pale yellow liquid, Yield: 30%.GC purity:
3
H
1
3
1
(
m, 5H),4.515 (s, 2H), 3.15 (s, 1H); C NMR (100 MHz,
99.67% H NMR (400 MHz, CDCl ) δ 3.55–3.58 (t, 2H),
3
H
CDCl ) δ 140.95, 128.54, 127.56, 127.07,64.93. GCMS;
2.59 (s, 1H), 1.461–1.532 (m, 2H), 1.284–1.376 (m, 2H),
3
C
+
13
M : Mol. formula: C H O, calculated:108.6, found:108.6.
0.864–0.901 (t, 3H); C NMR (100 MHz, CDCl ) δ 13.80,
7
8
3
C
+
1
8.86, 34.73, 62.41. GCMS;M : Mol. Formula: C H O,
4 10
4
-Butyl benzyl alcohol, 11b Pale yellow liquid, yield: 82%.
calculated: 74.00, found: 74.00.
1
GC purity: 96.56% H NMR (400 MHz, CDCl ) δ 7.37–
3
H
7
2
δ
.39 (d, J=8 Hz, 2H), 7.29–7.27 (d, J=8 Hz, 2H), 4.6 (s,
1-Phenyl-1-ethanol, 11i Colourless liquid, Yield: 65%.
1
3
1
H), 1.99 (s, 1H), 1.3 (s, 9H); C NMR (100 MHz, CDCl )
GC purity: 99.13% H NMR (400 MHz, CDCl ) δ 1.421–
3
3
H
31.39, 34.58,65.12, 125.51,126.94, 137.95, 150.71.
1.405 (d, J=6.4 Hz, 3H), 2.735 (s, 1H), 4.726–4.804 (m,
C
+
13
GCMS; M : Mol. formula: C H O, calculated:164.00,
1H), 7.203–7.305 (m, 5H); C NMR (100 MHz, CDCl ) δ
1
1
16
3
C
+
found: 164.00.
25.16, 70.26, 125.48, 127.41, 128.48, 145.92. GCMS; M :
Mol. Formula: C H O, calculated:122.0, found: 122.0.
8
10
4
-Methoxy benzyl alcohol, 11c Colourless oil. Yield: 75%.
1
GC purity: 98.28%, H NMR (400 MHz, CDCl ) δ 7.20–
1-Phenyl-1-propanol, 11j Yellow liquid. Yield: 75%. GC
3
H
1
7
3
5
.22 (d, 8 Hz, 2H), 6.82–6.84 (d, 8 Hz, 2H), 4.5 (s, 2H),
purity: 99.32%. H NMR (400 MHz, CDCl ) δ 0.855–0.892
3
H
1
3
.75 (s, 3H), 2.88 (s,1H); C NMR (100 MHz, CDCl ) δ
(t, 3H), 1.681–1.812 (m, 2H), 2.342 (s, 1H), 4.501–4.534 (t,
3
C
+
13
5.28, 64.64, 113.88, 128.66, 133.22, 159.04. GCM; M :
1H), 7.226–7.334 (m, 5H); C NMR (100 MHz, CDCl ) δ
3
C
+
Mol. Formula: C H O , calculated: 138.00, found: 138.00.
31.87, 75.97, 126.04, 127.46, 128.39, 144.64. GCMS; M :
8
10
2
Mol. Formula: C H O, calculated:136.00, found: 136.00.
9
12
4
-Hydroxy benzyl alcohol, 11d Colourless oil. Yield: 80%.
1
GC purity: 94.34%, H NMR (400 MHz, CDCl ) δ 6.95–
Cyclopentanol, 11k Colourless liquid. Yield: 80%.GC
3
H
1
6
1
δ
.93 (d, J=8 Hz, 2H), 6.68–6.70 (d, J=8 Hz, 2H), 5.37 (s,
purity: 99.57%, H NMR (400 MHz, CDCl ) δ 1.517 (s,
3
H
1
3
13
H), 4.63(s, 2H), 3.65 (s, 1H) C NMR (100 MHz, CDCl )
C
4H), 1.713 (s, 4H), 2.397 (s, 1H), 4.265 (s, 1H); C NMR
3
+
+
64.7,116.1,129.7,133.8,157.4. GCMS; M : Mol. For-
(100 MHz, CDCl ) δ 23.24, 35.40, 73.83. GCMS; M :
3
C
mula C H O , calculated: 124.00, found: 124.00.
Mol. Formula: C H O, calculated: 86.00, found: 86.00.
7
8
2
5 10
3
-Methoxy-4-hydroxy benzyl alcohol, 11e Colourless oil.
Cyclohexanol, 11l Colourless liquid, Yield: 83%. GC
1
1
Yield: 77%. GC purity: 95.21%, HNMR (400 MHz, CDCl )
purity: 99.57%. H NMR (400 MHz, CDCl ) δ 1.108–
3
3
H
δ 6.99 (s, 1H), 6.77–6.75 (d, J=8 Hz,1H), 6.57–6.55 (d,
1.229 (m, 5H), 1.496–1.523 (m, 1H), 1.689 (s, 1H), 1.857
H
1
3
J=8 Hz, 1H), 5.65 (s, 1H), 4.61 (s, 2H), 4.22 (s, 1H), 3.83
(s, 1H), 2.044–2.326 (m, 1H), 3.552–3.561 (s, 1H);
C
1
3
(
s, 3H), C NMR (100 MHz, CDCl ) δ 56.17,65.20,113
3 C
NMR (100 MHz, CDCl ) δ 22.14, 25.44, 35.48, 70.27.
3
C
+
+
.
80,115.6,118.71,138.10,147.33,149.02 GCMS; M : Mol.
GCMS;M : Mol. Formula: C H O, calculated: 100.00,
6 12
Formula C H O , calculated:154.0, found: 154.0.
found:100.00.
8
10
3
3
-Amino benzyl alcohol, 11f Light brown solid, Yield:
4-Methyl cyclohexanol, 11m Colourless liquid, yield: 79%.
1
5
5%, GC purity: 95.08%, MP 89–92 °C (92–94 °C, Litt).
GC purity: 99.38% HNMR (400 MHz, CDCl ) δ 0.96 (d,
3
H
1
13
HNMR (400 MHz, CDCl ) δ 7.13–7.11 (d, J=8 Hz, 2 H),
8 Hz, 3H), 1.27–1.72 (m, 9H), 3.17 (m, 1H), 1H CNMR
3
H
+
6
.56–6.58 (d, J=8 Hz, 2 H), 6.27 (s, 2H), 4.62 (s, 2H), 3.65
20.7, 29.6, 31.6, 34.0, 69.7. GCMS; M : Mol. Formula:
1
3
(
s, 1H). CNMR (100 MHz, CDCl ) 147.3, 131.2, 129.3,
C H O, calculated: 114.00, found: 114.0.
3
7
14
+
1
15.4, 64.7. GCMS; M : Mol. Formula: C H NO, calcu-
7
9
lated:123.0, found:123.0.
Cyclododecanol, 11n Colourless solid, yield: 82%. GC
1
purity: 98.6%. MP 89–92 °C, (92–94 °C, Litt). H NMR
6
-Methoxy-2, 6-dimethylheptyl alcohol, 11g
(400 MHz, CDCl ) δ 1.344–1.676 (m, 23H), 3.828–3.853
3
H
1
3
(
t, 1H); C NMR (100 MHz, CDCl ) δ 21.58, 21.93, 28.98,
3 C
1
+
Colourless oil. Yield: 50%.GC purity: 98.35% H NMR
400 MHz, CDCl ) δ 0.867–0.882 (d, J = 6 Hz, 3H),
31.06, 31.76, 32.10, 33.04, 35.51, 66.84, 70.79. GCMS; M :
(
Mol. Formula: C H O, calculated: 184.00, found:184.00.
3
H
12 24
1
3