Kumar et al.
723
13C NMR spectra were recorded in CDCl3 and DMSO-d6 us-
ing TMS as an internal standard on a JEOL spectrometer at
500 MHz and 125 MHz, respectively. Mass spectra were re-
corded on a Thermo Finnigan LCQ Advantage MAX 6000
ESI spectrometer. Column chromatography was performed
on silica gel (100–200 mesh, SRL, India). Analytical TLC
was performed on precoated aluminium sheets of silica gel
G/UV-254 of 0.2 mm thickness (Merck, Germany).
Acetophenone (98–86–2)
1
Colourless liquid. H NMR (500 MHz, CDCl3) δ: 2.56 (s,
3H), 7.42 (t, J = 7.5 Hz, 1H), 7.52 (d, J = 8.0 Hz, 2H), 7.92
(d, J = 7.5 Hz, 2H). 13C NMR (125 MHz, CDCl3) δ: 26.69,
128.38, 128.66, 133.21, 137.16, 198.30. MS m/z = 120 M+.
2-Nitroacetophenone (577–59–3)
1
Yellow liquid. H NMR (500 MHz, CDCl3) δ: 2.51 (s,
3H), 7.41 (dd, J = 1.5, 7.6 Hz, 1H), 7.55–7.58 (m, 1H), 7.69
(dt, J = 1.5, 7.6 Hz, 2H), 8.02 (d, J = 8.4 Hz). 13C NMR
(125 MHz, CDCl3) δ: 30.18, 124.40, 127.43, 130.81,
134.37, 137.88, 145.82, 200.00. MS m/z = 165 M+.
Representative procedure for oxidation of primary and
secondary alcohols to aldehydes and ketones
To 1.30 mmol of 3-(4-chlorophenyl)-1-phenylprop-2-en-1-ol
in ethylacetate/water (7:3) (10 mL) was added TEMPO (0.02
equiv.), and the reaction mixture was stirred at room temper-
ature. After 5 min, FeCl3@6H2O (1.69 mmol) was added, and
stirring continued, following the progress of the reaction by
TLC. After completion of the reaction, ethyl acetate layer
was separated, and the aqueous layer was extracted with
ethyl acetate (3 × 3 mL). Organic layers were combined and
dried with sodium sulphate, filtered, and concentrated under
reduced pressure.The residue thus obtained was purified by
column chromatography to obtain the (2E)-3-(4-
chlorophenyl)-1-phenylprop-2-en-1-one.
4-Methoxyacetophenone (100–06–1)
Colourless solid (petroleum ether); mp 36 °C (lit. (18) 38–
39 °C). 1H NMR (500 MHz, CDCl3) δ: 2.56 (s, 3H), 3.87 (s,
3H), 6.94 (d, J = 8.4 Hz, 2H), 7.94 (d, J = 8.4 Hz, 2H).
13C NMR (125 MHz, CDCl3) δ: 26.48, 56.62, 113.84,
127.42, 130.72, 163.60, 196.92. MS m/z = 150 M+.
4-Bromoacetophenone (99–90–1)
White solid (petroleum ether); mp 51 °C (lit. (20) 51–
52 °C). 1H NMR (500 MHz, CDCl3) δ: 2.58 (s, 3H), 7.60 (d,
J = 8.4 Hz, 2H), 7.81 (d, J = 8.4 Hz, 2H). 13C NMR
(125 MHz, CDCl3) δ: 26.64, 128.40, 129.93, 131.99, 135.91,
197.14. MS m/z = 198 M+.
Benzaldehyde (100–52–7)
1
Colourless liquid. H NMR (500 MHz, CDCl3) δ: 7.49 (t,
J = 7.7 Hz, 2H), 7.59 (t, J = 6.9 Hz, 1H), 7.84 (d, J =
7.7 Hz, 2H), 9.98 (s, 1H). 13C NMR (125 MHz, CDCl3) δ:
129.08, 129.81, 134.56, 136.45, 192.52. MS m/z = 106 M+.
4-Ethoxyacetophenone (1676–63–7)
Colourless solid (petroleum ether); mp 39 °C (lit. (18) 36–
1
37 °C). H NMR (500 MHz, CDCl3) δ: 1.42 (t, J = 6.9 Hz,
3H), 2.56 (s, 3H), 4.08 (q, J = 6.9 Hz, 2H), 6.90 (d, J =
9.1 Hz, 2H), 7.91 (d, J = 8.4 Hz, 2H). 13C NMR (125 MHz,
CDCl3) δ: 14.75, 26.42, 63.83, 114.19, 130.22, 130.68,
163.00, 196.90. MS m/z = 164 M+.
2-Nitrobenzaldehyde (552–89–6)
White solid (toluene/petroleum ether); mp 43 °C (lit. (18)
1
43–44 °C). H NMR (500 MHz, CDCl3) δ: 7.73–7.78(m,
2H), 7.91 (d, J = 9.5 Hz, 1H), 8.09 (d, J = 8.0 Hz, 1H),
10.38 (s, 1H). 13C NMR (125 MHz, CDCl3) δ: 124.58,
129.71, 131.40, 133.84, 134.21, 149.63, 188.29. MS m/z =
151 M+.
(2E)-3-(4-Chlorophenyl)-1-phenylprop-2-en-1-one
White solid (absolute ethanol); mp 110 °C (lit. (21) 111–
113 °C). 1H NMR (500 MHz, CDCl3) δ: 7.48 (d, J = 6.9 Hz,
2H), 7.53 (t, J = 6.9 Hz, 2H), 7.63 (t, J = 6.9 Hz, 1H), 7.70
(d, J = 16.0 Hz, 1H), 7.88–7.94 (m, 3H), 8.12 (d, J = 7.6 Hz,
2H). 13C NMR (125 MHz, CDCl3) δ: 123.27, 129.11,
129.33, 129.48, 131.13, 133.77, 134.15, 135.66, 137.96,
143.07, 189.60. MS m/z = 243 M+. Anal. calcd. for
C15H11ClO (242.70): C, 74.23; H, 4.57; Cl, 14.61. Found: C,
74.28; H, 4.52; N, 14.69.
3-Nitrobenzaldehyde (99–61–6)
Yellow solid (toluene/petroleum ether); mp 56 °C (lit.
1
value (18) 58 °C). H NMR (500 MHz, CDCl3) δ: 7.76 (t,
J = 8.4 Hz, 1H), 8.22 (d, J = 7.5 Hz, 1H), 8.47 (d, J =
7.0 Hz, 1H), 8.69 (d, J = 1.5 Hz, 1H), 10.11 (s, 1H). 13C
NMR (125 MHz, CDCl3) δ: 124.53, 128.69, 130.51, 134.80,
137.45, 148.83, 189.90. MS m/z = 151 M+.
9-Anthraldehyde (642–31–9)
4-Nitrobenzaldehyde (555–16–8)
Pale yellow solid (ethyl acetate/petroleum ether); mp
105 °C (lit. value (19) 104–106 °C). H NMR (500 MHz,
CDCl3) δ: 8.06 (d, J = 8.4 Hz, 2H), 8.36 (d, J = 8.4 Hz, 2H),
10.14 (s, 1H). 13C NMR (125 MHz, CDCl3) δ: 124.38,
130.58, 140.13, 151.18, 190.49. MS m/z = 151 M+.
Yellow solid; (aq. acetic acid); mp 104 °C (lit. (18) 104–
1
105 °C). H NMR (500 MHz, CDCl3) δ: 7.54 (t, J = 6.9 Hz,
1
2H), 7.67 (t, J = 7.6 Hz, 2H), 8.04 (d, J = 8.4 Hz, 2H), 8.66
(s, 1H), 8.97 (d, J = 9.2 Hz, 2H), 11.50 (s, 1H). 13C NMR
(125 MHz, CDCl3) δ: 123.62, 124.77, 125.79, 129.23,
129.38, 131.15, 132.22, 135.35, 193.12. MS m/z = 206 M+.
4-Chlorobenzaldehyde (104–88–1)
2-Cyclohexenone (930–68–7)
Brown liquid. H NMR (500 MHz, CDCl3) δ: 1.90–1.95
(m, 2H), 2.24–2.28 (m, 2H), 2.31–2.34 (m, 2H), 5.90–5.92
(m, 1H), 6.89–6.93 (m, 1H). 13C NMR (125 MHz, CDCl3)
δ: 22.73, 25.69, 38.10, 129.85, 150.92, 199.86. MS m/z = 96
M+.
1
White solid (petroleum ether); mp 45 °C (lit. (19) 45–
1
46 °C). H NMR (500 MHz, CDCl3) δ: 7.49 (d, J = 8.6 Hz,
2H), 7.80 (d, J = 8.0 Hz, 2H), 9.95 (s, 1H). 13C NMR
(125 MHz, CDCl3) δ: 129.53, 130.99, 134.77, 141.02,
190.97. MS m/z = 141 M+.
© 2008 NRC Canada