Molecules 2019, 24, 100
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1
1-(3-Methylphenyl)ethanone (colorless oil, yield 93%): H-NMR (500 MHz, CDCl3)
δ
7.77–7.74(m, 2H),
7.38–7.33 (m, 2H), 2.59 (s, 3H), 2.41 (s, 3H). 13C-NMR (125 MHz, CDCl3)
128.7, 128.4, 125.5, 26.6, 21.2. GC-MS (EI): m/z: 134.10 [M+].
δ 198.3, 138.3, 137.1, 133.8,
1
1-(2-Methylphenyl)ethanone (colorless oil, yield 95%): H-NMR (500 MHz, CDCl3)
δ
7.71–7.69(m, 1H),
7.40–7.36 (m, 1H), 7.28–7.24 (m, 2H), 2.58 (s, 3H), 2.54 (s, 3H). 13C-NMR (125 MHz, CDCl3)
138.3, 137.6, 132.0, 131.5, 129.3, 125.6, 29.5, 21.5. GC-MS (EI): m/z: 134.09 [M+].
δ 201.7,
1
1-(4-Methoxyphenyl)ethanone (colorless oil, yield 89%): H-NMR (500 MHz, CDCl3)
δ
7.94–7.91 (m, 2H),
6.94–6.91 (m, 2H), 3.86 (s, 3H), 2.55 (s, 3H). 13C-NMR (125 MHz, CDCl3)
δ 196.7, 163.5, 130.5, 130.3,
113.6, 55.4, 26.3. GC-MS (EI): m/z: 150.14 [M+].
1
1-(4-Nitrophenyl)ethanone (yellow crystal powder, yield 90%): H-NMR (500 MHz, CDCl3)
δ
8.28–8.27
(m, 2H),
δ
8.11–80.08 (m, 2H),
δ
2.66 (s, 3H); 13C-NMR (125 MHz, CDCl3)
δ
196.3, 150.3, 141.3, 129.2,
123.7, 26.9. GC-MS (EI): m/z: 165.05 [M+].
1
Propiophenone (colorless oil, yield 88%): H-NMR (500 MHz, CDCl3)
δ 7.99–7.97 (m, 2H), 7.58–7.55(m,
1H), 7.49–7.45 (m, 2H), 3.04–3.00 (m, 2H), 1.24 (t, J = 7.2 Hz, 3H). 13C-NMR (125 MHz, CDCl3)
137.0, 132.9, 128.6, 128.0, 31.8, 8.3. GC-MS (EI): m/z: 134.16 [M+].
δ 200.9,
1
Phenylbutanone (colorless oil, yield 92%): H-NMR (500 MHz, CDCl3)
δ 7.95–7.93 (m, 2H), 7.54–7.50(m,
1H), 7.44–7.41 (m, 2H), 2.94–2.91 (m, 2H), 1.79–1.72 (m, 2H), 0.99 (t, J = 7.4 Hz, 3H). 13C-NMR (125 MHz,
CDCl3) δ 200.2, 137.0, 132.7, 128.4, 127.9, 40.3, 17.6, 13.7. GC-MS (EI): m/z: 148.17 [M+].
2-Methylpropiophenone (colorless oil, yield 89%): 1H-NMR (500 MHz, CDCl3)
δ 7.98–7.96 (m, 2H),
7.58–7.54 (m, 1H), 7.49–7.46 (m, 2H), 3.60–3.54 (m, 1H), 1.23 (d, J = 6.9 Hz, 6H). 13C-NMR (125 MHz
CDCl3) δ 204.5, 136.3, 132.8, 128.6, 128.3, 35.3, 19.1. GC-MS (EI): m/z: 148.18 [M+].
,
1-(4-Methylphenyl)propan-2-one (colorless oil, yield 93%): 1H-NMR (500 MHz, CDCl3)
δ 7.87 (d,
J = 8.2 Hz, 2H), 7.28–7.25 (m, 2H), 3.00–2.96 (m, 2H), 2.41 (s, 3H), 1.22 (t, J = 7.3 Hz, 3H). 13C-NMR
(125 MHz, CDCl3) δ 200.5, 143.5, 134.4, 129.2, 128.1, 31.6, 21.5, 8.3. GC-MS (EI): m/z: 148.16 [M+].
1
1-Tetralone (white solid, yield 90%): H-NMR (500 MHz, CDCl3)
δ 8.04–8.03 (m, 1H), 7.48–7.45 (m, 1H),
7.30 (t, J = 7.5 Hz, 1H), 7.25 (d, J = 7.6 Hz, 1H), 2.97 (t, J = 6.1 Hz, 2H), 2.67–2.64 (m, 2H), 2.17–2.12 (m,
2H). 13C-NMR (125 MHz, CDCl3)
(EI): m/z: 146.17 [M+].
δ
198.3, 144.4, 133.3, 132.6, 128.7, 127.1, 126.6, 39.1, 29.7, 23.2. GC-MS
1
Benzophenone (white solid, yield 95%): H-NMR (500 MHz, CDCl3)
J = 7.4 Hz, 2H), 7.49 (t, J = 7.6 Hz, 4H). 13C-NMR (125 MHz, CDCl3)
GC-MS (EI): m/z: 182.00 [M+].
δ
δ
7.82 (d, J = 7.4 Hz, 4H), 7.60 (t,
196.7, 137.6, 132.4, 130.0, 128.2.
1
1-(Thiophen-2-yl)ethanone (yellow oil, yield 80%): H-NMR (500 MHz, CDCl3)
7.63–7.62 (m, 1H), 7.12–7.10 (m, 1H), 2.55 (s, 3H). 13C-NMR (125 MHz, CDCl3)
132.4, 128.0, 26.8. GC-MS (EI): m/z: 125.97 [M+].
δ
δ
7.69–7.68 (m, 1H),
190.6, 144.5, 133.7,
1
Cycloheptanone (colorless oil, yield 57%): H-NMR (500 MHz, CDCl3)
δ 2.49–2.47 (m, 4H), 1.70–1.64 (m,
8H); 13C-NMR (125 MHz, CDCl3) δ 215.3, 43.8, 30.4, 24.3. GC-MS (EI): m/z: 112.11 [M+].
4. Conclusions
In conclusion, the electrochemical behaviour of the nitroxyl radical ABNO for the oxidation
of 1-phenylethanol in acetonitrile solution have been studied. The electrochemical measurements
revealed that ABNO showed reversible redox behavior and it had lower potential than TEMPO.
The oxoammonium ion (ABNO+) was generated by single-electron oxidation. According to the in situ
FTIR spectra results, the base 2,6-lutidine received a hydrogen proton to become 2,6-lutidinium cation,
which was a crucial process during the synthesis of acetophenone from 1-phenylethanol. Under mild