2274
A. T. Khan et al. / Tetrahedron Letters 48 (2007) 2271–2274
10. Das, S.; Bhowmick, T.; Punniyamurthy, T.; Dey, D.;
Nath, J.; Chaudhuri, M. K. Tetrahedron Lett. 2003, 44,
4915–4917.
features of the present method include the ease of oper-
ation, high efficiency and mild conditions.
11. Valusamy, S.; Punniyamurthy, T. Tetrahedron Lett. 2003,
44, 8955–8957.
12. Nechab, M.; Einhorn, C.; Einhorn, J. Chem. Commun.
2004, 1500.
Acknowledgements
13. Bonvin, Y.; Callens, E.; Larrosa, I.; Henderson, D. A.;
Oldham, J.; Burton, A. J.; Barrett, A. G. M. Org. Lett.
2005, 7, 4549–4552.
14. Shaikh, T. M. A.; Emmanuvel, L.; Sudalai, A. J. Org.
Chem. 2006, 71, 5043–5046.
15. (a) Khan, A. T.; Goswami, P. Tetrahedron Lett. 2005, 46,
4937–4940; (b) Khan, A. T.; Goswami, P.; Choudhury, L.
H. Tetrahedron Lett. 2006, 47, 2751–2754.
We thank the IITG for a research fellowship to T.P. and
the CSIR, New Delhi, for a research fellowship to
L.H.C. We are grateful to the Director, IITG, for
providing research facilities. We are grateful for the
referee’s valuable comments and suggestions.
16. Typical experimental procedure: To a stirred solution of
alkyl-arene (5 mmol) and aq 48% HBr (0.5 mL,
4.30 mmol) in 5 mL of dichloromethane was added 30%
H2O2 (3 mL, 25 mmol) at room temperature. The reaction
mixture was stirred at room temperature and the progress
of the reaction was monitored by TLC. After completion,
saturated aqueous sodium metabisulfite solution (2 mL)
was added and the reaction mixture was extracted with
dichloromethane (2 · 20 mL). The combined organic
extract was washed with water then brine (1 · 10 mL)
and dried over anhydrous sodium sulfate. The organic
layer was concentrated on a rotavapour and the crude
residue was passed through a silica gel column to obtain
the pure products. 2-Benzoyl ethanol 2i: 1H NMR (CDCl3,
400 MHz): 2.33 (br s, 1H, D2O exchangeable), 3.23 (t,
J = 5.6 Hz, 2H), 4.02 (t, J = 5.6 Hz, 2H), 7.45 (t,
J = 7.6 Hz, 2H), 7.54–7.58 (m, 1H), 7.94 (d, J = 7.6 Hz,
2H); 13C NMR (CDCl3,100 MHz): 40.5, 58.1, 127.9 (2C),
128.5 (2C), 133.4, 136.5, 200.1; IR (neat): 3411 (OH), 1685
(CO) cmÀ1; Anal. Calcd. for C9H10O2 (150.18): C, 71.98;
H, 6.71. Found: C, 71.72; H, 6.79.
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