Page 5 of 5
RSC Advances
DOI: 10.1039/C5RA14563E
Journal Name
ARTICLE
4
5
F. L. Lam, T. T-L. Au-Yeung, F. Y. Kwong, Z. Zhou, K. Y. Wong
and A. S. C. Chan, Angew. Chem. Int. Ed., 2008, 47, 1280.
(a) A. Prades, R. Corberán, M. Poyatos and E. Peris, Chem.
Eur. J., 2008, 14, 11474; (b) T. Mitsudome, T. Matsuno, S.
Sueoka, T. Mizugaki, K. Jitsukawa and K. Kaneda, Green
Chem., 2012, 14, 610; (c) J. S. Yadav, D. C. Bhunia, K. V.
Krishna and P. Srihari, Tetrahedron Lett., 2007, 48, 8306.
J-L. Yu, H. Wang, K-F. Zou, J-R. Zhang, X. Gao, D-W. Zhang
and Z-T. Li, Tetrahedron, 2013, 69, 310.
Bromodimethylsulfonium bromide BDMS (0.2 mmol) was
added to a mixture of benzaldehyde (2.0 mmol) and 2-
naphthol (2.0 mmol) in 5 mL of acetonitrile and the reaction
mixture was kept for stirring at room temperature. Then, 4-
methylthiophenol (2.0 mmol) was added to it and the progress
of the reaction was monitored by TLC. After 6 h of stirring, 2.0
mmol of ethanol (120 μL) and 1 equivalent BDMS were added
into it and the reaction completed instantly. Then, acetonitrile
was removed in a rotatory evaporator and the residue was
extracted with dichloromethane (1 x 25 mL) and washed with
aqueous sodium bicarbonate. The organic layer was washed
with water and dried over anhydrous sodium sulfate. On
concentration followed by purification through a silica gel
column, the desired product 3a was obtained.
6
7
(a) X. J. Sun, J. F. Zhou and P. S. Zhao, J. Heterocyclic Chem.,
2011, 48, 1347; (b) J. M. Khurana, B. Nand and S. Sneha, J.
Heterocyclic Chem., 2011, 48, 1388.
8
9
(a) A. T. Khan, S. Ali, A. A. Dar and M. Lal, Tetrahedron Lett.,
2011, 52, 5157; (b) A. Hassanabadi, J. Chem. Res., 2013, 152.
(a) A. R. Katritzky and X. Lan, Synthesis, 1992, 761; (b) A. K.
III. Synthesis of 1-(hydroxy(aryl)methyl)naphthalen-2-ol (7)
Shaikh, A. J. A. Cobb and G. Varvounis, Org. Lett., 2012, 14
,
Into a 25 mL round bottom flask was taken 1 mmol of 1 in 2 mL
584; (c) S. Arumugam and V. V. Popik, J. Am. Chem. Soc.,
2011, 133, 15730; (d) S. Arumugam and V. V. Popik, J. Am.
Chem. Soc., 2011, 133, 5573.
of CH3CN. To this reaction mixture, 40 µL of water and 1
equivalent of BDMS were added successively and the reaction
mixture was stirred at room temperature for 5 minutes and
the progress of the reaction was monitored by TLC. After
completion of the reaction, the mixture was concentrated in a
rotatory evaporator and the crude residue was extracted with
DCM (1 x 25 mL) and washed with water. The organic layer
was dried over Na2SO4 and it was concentrated in vacuo. The
10 (a) C. F. Nising and S. Brӓse, Chem. Soc. Rev., 2012, 41, 988;
(b) C. F. Nising and S. Brӓse, Chem. Soc. Rev., 2008, 37, 1218.
11 (a) E. Mondal, G. Bose and A. T. Khan, Synlett, 2001, 785; (b)
E. Mondal, G. Bose, P. R. Sahu and A. T. Khan, Chem. Lett.,
2001, 1158.
12 (a) P. M. B. Barua, P. R. Sahu, E. Mondal, G. Bose and A. T.
Khan, Synlett, 2002, 81; (b) E. Mondal, P. M. B. Barua, G.
Bose and A. T. Khan, Chem. Lett., 2002, 210.
pure product
through a silica gel (60-120 mesh) column chromatography.
Similarly, were obtained by following identical reaction
procedure.
7 was obtained in good yield after purification
9
13 (a) A. T. Khan, A. Choudhury, S. Ali and M. M. Khan,
Tetrahedron Lett., 2012, 53, 4852; (b) A. T. Khan, A. Ali, P.
Goswami and L. H. Choudhury, J. Org. Chem., 2006, 71, 8961;
(c) S. Bhattacharjee, D. K. Das and A. T. Khan, Tetrahedron
Lett., 2015, 56, 2412; (d) A. T. Khan, R. S. Basha, M. Lal and
Acknowledgements
KI is thankful to UGC for his research fellowship. RSB is grateful
to CSIR for Research Associate Fellowship. AAD is thankful to
IIT Guwahati for his research fellowship. DKD acknowledges to
CSIR, New Delhi for SRF. ATK acknowledge CSIR, New Delhi for
financial supports grant no.: 02(0181)/14/EMR-II. We
acknowledge SerajulHaqueFaizi and Mohammad Hedayetullah
Mir for important suggestion for analyzing crystallographic
data. The authors are grateful to the Director, IIT Guwahati for
providing general facilities to carry out the research work. We
are thankful to DST for providing XRD facility under the FIST
programme.
M. H. Mir, RSC Adv., 2012, 2, 5506; (e) A. T. Khan, R. S. Basha
and M. Lal, Tetrahedron Lett., 2012, 53, 2211; (f) A. T.Khan
andM. M. Khan, Carbohydr. Res. 2010, 345, 2139; (g) L. H.
Choudhury, T. Parvin and A. T. Khan, Tetrahedron, 2009, 65
,
9513; (h) A. T. Khan, T. Parvin and L. H. Choudhury, J. Org.
Chem., 2008, 73, 8398.
14 (a) S. Gazi and R. Ananthakrishnan, RSC Adv. 2012, 2, 7781;
(b) D. K. Yadav, R. Patel, V. P. Srivastava, G. Watal and L. D. S.
Yadav, Tetrahedron Lett. 2010,51, 5701;(c)L. D. S. Yadav, R.
Patel and V. P. Srivastava, Tetrahedron Lett. 2010,51, 739; (d)
B. Jiang, Y. Dou, X. Xu and M. Xu, Org. Lett. 2008, 10, 593; (e)
D. S. Bhalerao and K. G. Akamanchi, Synlett 2007, 2952; (f) B.
Das, Y. Srinivas, H. Holla, K. Laxminarayana and R. Narender,
Tetrahedron Lett. 2007, 48, 6681.
Notes and references
1
2
3
(a) J. Buckingham, Dictionary of Natural Products, University:
Cambridge, MA, 1994; (b) T. F. Woiwode, C. Rose and T. J.
Wandless, J. Org. Chem., 1998, 63, 9594.
15 H. Loghmani-Khouzani, M. R. Poorheravi, M. M. M. Sadeghi,
(a) A. V. Ambade and A. Kumar, Prog. Polym. Sci., 2000, 25
,
L. Caggiano and R. F. W. Jackson, Tetrahedron, 2008, 64
,
1141; (b) M. Beldi, R. Medimagh, S. Chatti, S. Marque, D.
Prim, A. Loupy and F. Delolme, Eur. Polym. J., 2007, 43, 3415.
(a) L. G. Wade, Organic Chemistry, 5th ed., Pearson
Education, Inc. London, 2005; (b) E. Fuhrmann and J.
7419.
16 (a) L-Z. Dai, M-J. Qi, Y-L. Shi, X-G. Liu and M. Shi, Org. Lett.,
2007, , 3191; (b) T. Hirabayashi, Y. Okimoto, A. Saito, M.
Morita, S. Sakaguchi and Y. Ishii, Tetrahedron, 2006, 62
9
,
,
Talbiersky, Org. Process Res. Dev., 2005, 9, 206.
2331; (c) M. Koskinen and K. Hemminki, Org. Lett., 1999,
1
1233.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5