1088
I. Mohammadpoor-Baltork et al.
Table 10 continued
Entry
R
MOM ether
EOM ether
MW irradiation
(method A)
Traditional method
(method B)
MW irradiation
(method A)
Traditional method
(method B)
Time (min) Yield (%)a Time (min) Yield (%)a Time (min) Yield (%)a Time (min) Yield (%)a
17
18
19
a
CH3(CH2)6CH2 2.5
94
90
87
60
135
180
86
83
74
2.5
6.5
8
91
88
85
60
135
180
84
80
75
(?)-Menthyl
7
8
2-Adamantyl
Isolated yield
2. Greene TW, Wuts PGM (2006) Greene’s protective groups in
organic chemistry, 4th edn. Wiley Interscience, New York
3. Meyers AI, Durandetta JL, Munavu R (1975) J Org Chem
40:2021
with the aid of ATCFO sensor TS3517 inserted directly
into the corresponding reaction container.
Deprotection of 4-chlorobenzyl methoxymethyl ether
to 4-chlorobenzyl alcohol: typical procedure
4. Kleczykowski GR, Schlessinger RH (1978) J Am Chem Soc
100:1938
5. Boehlow TR, Harburn JJ, Spilling CD (2001) J Org Chem
66:3111
A mixture of 1 mmol 4-chlorobenzyl methoxymethyl ether
and 0.5 mmol [Hmim][HSO4] was stirred at 50 °C or
exposed to microwave irradiation (150 W). After the
reaction was completed (detected by TLC), the reaction
mixture was cooled to room temperature and Et2O
(2 9 10 cm3) was added. The organic layer was washed
with 10 cm3 H2O and dried over anhydrous Na2SO4. The
solvent was evaporated and the crude product was purified
by column chromatography on neutral alumina (eluent: n-
hexane/ethyl acetate, 4:1) to afford the pure 4-chlorobenzyl
alcohol [30] (Table 3, entry 9).
6. Ramesh C, Ravindranath N, Das B (2003) J Org Chem 68:7101
7. Peng Y, Ji C, Chen Y, Huang C, Jiang Y (2004) Synth Commun
34:4325
8. Oriyama T, Watahiki T, Kobayashi Y, Hirano H, Suzuki T (2001)
Synth Commun 31:2305
9. Khalafi-Nezhad A, Alamdari RF (2001) Tetrahedron 57:6805
10. Reddy SV, Rao RJ, Kumar US, Rao JM (2003) Chem Lett
32:1038
11. Sabatha G, Babu SR, Rajkumar M, Srividya R, Yadav JS (2001)
Org Lett 3:1149
12. Deville JP, Bahar V (2001) J Org Chem 66:4097
13. Sharma GVM, Reddy KL, Lakshmi PS, Krishna PR (2004)
Tetrahedron Lett 45:9229
14. Corey EJ, Gras J-L, Ulrich P (1976) Tetrahedron Lett 17:809
15. Boeckman RK Jr, Potenza JC (1985) Tetrahedron Lett 26:1407
16. Davis JH Jr (2004) Chem Lett 33:1072
17. Cocalia VA, Gutowski KE, Rogers RD (2006) Coord Chem Rev
250:755
Direct transformation of 4-chlorobenzyl methoxymethyl
ether to 4-chlorobenzyl acetate and
(4-chlorobenzyloxy)trimethylsilane: typical procedure
18. Leadbeater NE, Torenius MH, Tye H (2004) Comb Chem High
Throughput Screen 7:511
¨
19. Wasserscheid P, Van Hal R, Bosmann A (2002) Green Chem
A mixture of 1 mmol 4-chlorobenzyl methoxymethyl ether,
3 mmol Ac2O or HMDS, and 0.5 mmol [Hmim][HSO4]
was stirred at 50 °C or exposed to microwave irradiation
(150 W). The progress of the reaction was monitored by
TLC (eluent: n-hexane/ethyl acetate, 4:1). After completion
of the reaction, the excess amounts of Ac2O or HMDS were
evaporated and Et2O (2 9 10 cm3) was added. The organic
layer was washed with 10 cm3 H2O and dried over anhy-
drous Na2SO4. Evaporation of the solvent followed by
column chromatography on neutral alumina afforded the
pure 4-chlorobenzyl acetate or (4-chlorobenzyloxy)tri-
methylsilane (Tables 9, 10, entry 9).
4:400
20. Mehdi H, Bodor A, Lantos D, Horvath IT, De Vos DE, Binne-
mans K (2007) J Org Chem 72:517
`
21. Mogadam M, Tangestaninejad S, Mirkhani V, Mohammadpoor-
Baltork I, Taghavi SA (2007) Catal Commun 8:2087
22. Mohammadpoor-Baltork I, Moghadam M, Tangestaninejad S,
Mirkhani V, Hojati SF (2008) Polyhedron 27:750
23. Khosropour AR, Mohammadpoor-Baltork I, Ghorbankhandi H
(2006) Catal Commun 7:713
24. Khosropour AR, Mohammadpoor-Baltork I, Ghorbankhani H
(2006) Tetrahedron Lett 47:3561
25. Shirini F, Zolfigol MA, Safari A (2006) J Chem Res (S) 154
26. Reddy CS, Smitha G, Chandrasekhar S (2003) Tetrahedron Lett
44:4693
27. Karimi B, Golshani B (2000) J Org Chem 65:7228
28. Maity G, Roy SC (1993) Synth Commun 23:1667
29. Mohammadpoor-Baltork I, Mogahdam M, Tangestaninejad S,
Mirkhani V, Mirjafari A (2008) Can J Chem 86:831
30. Mohammadpoor-Baltork I, Mogahdam M, Tangestaninejad S,
Mirkhani V, Mirjafari A (2008) Polyhedron 27:2612
Acknowledgments The authors are grateful to the Center of
Excellence of Chemistry and Research Council of University of
Isfahan for financial support of this work.
References
1. Kocienski PJ (1994) Protecting groups. Thieme, Stuttgart
123