and rinsed thrice with ethanol (30 mL), and was then dried under
vacuum overnight. The loading of the catalyst was determined
to be 0.54 mmol g-1 by elemental analysis.
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General procedure for the synthesis of benzoxanthenes
A mixture of aldehyde (2 mmol), 2-naphthol (2 mmol), dime-
done (2.4 mmol) and AIL@MNP (55 mg) was stirred at 90 ◦C
in an oil bath for 35–65 min, as indicated by TLC for a complete
reaction. Ethyl acetate was added and the catalyst was separated
magnetically from the product solution, washed with ethyl ac-
etate, and used for subsequent cycles after drying under vacuum.
Pure amidoalkyl naphthols were afforded by evaporation of
the solvent, followed by recrystallization from ethanol or by
column chromatography on silica gel using ethyl acetate/hexane
as the eluent. The naphthols were characterized by the use of
spectral data and comparison of their physical data with the lit-
erature. Spectral data for 12-(4-hydroxy-3-methoxy-phenyl)-9,9-
dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one (Table 2,
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1
entry 14): H NMR (500 MHz, CDCl3) d 8.01 (d, J = 8.4 Hz,
1H), 7.79 (dd, J = 13.8, 8.4 Hz, 2H), 7.48–7.44 (m, 1H), 7.42–
7.39 (m, 1H), 7.34 (d, J = 8.9 Hz, 1H), 7.03 (s, 1H), 6.68 (m, 2H),
5.66 (s, 1H), 5.46 (s, 1H), 3.85 (s, 3H), 2.58 (s, 2H), 2.35–2.27
(m, 2H), 1.14 (s, 3H), 1.00 (s, 3H); 13C NMR (125 MHz, CDCl3)
d 197.1, 163.8, 147.8, 146.1, 143.8, 137.0, 131.5, 131.4, 128.8,
128.4, 127.0, 124.9, 123.7, 121.0, 117.8, 117.0, 114.5, 114.1,
111.3, 55.9, 50.9, 41.4, 34.2, 32.3, 29.3, 27.2; ESI-MS: m/z =
401 [M + H]; Anal. calc. for C26H24O4: C, 77.98; H, 6.04. Found:
C, 78.06; H, 6.10.
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Acknowledgements
We are grateful for the financial support from the Natu-
ral Science Foundation of Jiangsu Province of China (No.
BK2010485), the Doctoral Fund of Ministry of Education of
China for New Teacher (No. 20082881029), and the Science
and Technology Development Fund of Nanjing University of
Science and Technology (No. XKF09066).
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