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6465
1970, 13, 203±205. (b) Crenshaw, R. R.; Luke, G. M.; Bialy, G.
J. Med. Chem. 1972, 15, 1179±1180. (c) Goudie, A. C.; Gaster,
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A gram-scale synthesis of 2-acetyl-6-methoxynaphtha-
lene. To a mixture of 2-methoxynaphthalene (1.634 g,
10.3 mmol) and LiClO4 (6.593 g, 62.0 mmol) in MeNO2
(10 mL), Sb(OTf)3 (0.294 g, 0.5 mmol, 5 mol%) was
added. Acetic anhydride (1.266 g, 12.4 mmol) was slowly
added at 508C for 5 min, and the reaction mixture was stir-
red at 508C for 5 h. After the mixture was poured into
saturated aqueous NaHCO3 (50 mL), the mixture was
extracted with Et2O (100 mL£2) and the combined organic
phase was washed with H2O (50 mL£2). The organic
extract was dried with anhydrous Na2SO4, ®ltered, and
evaporated to give a crude oil. This crude product was
treated with activated charcoal in AcOEt, and then ®ltered.
The solvent was removed and the residue was recrystallized
from heptane to afford 2-acetyl-6-methoxynaphthalene
(1.542 g, 7.70 mmol, 75%).
2. (a) Sonawane, H. R.; Bellur, N. S.; Ahuja, J. R.; Kulkarni, D. G.
Tetrahedron: Asymmetry 1992, 3, 163±191. (b) Zoeller, J. R.;
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K.; Ohara, Y.; Iizumi, T.; Takakuwa, Y. Tetrahedron Lett. 1983,
24, 1531±1534.
3. (a) Gore, P. H. Friedel Crafts and Related Reactions; Olah,
G. A., Ed.; Wiley Interscience: New York, 1964; Vol. III, p 72.
(b) Girdler, R. B.; Gore, P. H.; Hoskins, J. A. J. Chem. Soc. C 1966,
181±185. (c) Dowdy, D.; Gore, P. H.; Waters, D. N. J. Chem. Soc.
Perkin 2 1991, 1149±1159.
4. Davenport, K. G.; Linstid, H. C., III U.S. Pat. 4,593,125, 1986.
5. Pivsa-Art, S.; Okuro, K.; Miura, M.; Murata, S.; Nomura, M.
J. Chem. Soc., Perkin Trans. 1 1994, 1703±1707.
2-Acetyl-6-methoxynaphthalene. A pale yellow crystal.
Mp 104.5±1068C (lit.3b 106.58C). 1H NMR (CDCl3): d
2.71 (s, 3H), 3.96 (s, 3H) 7.16 (d, J2.6 Hz, 1H), 7.21
(dd, J8.8, 2.6 Hz, 1H), 7.77 (d, J8.6 Hz, 1H), 7.86 (d,
J8.8 Hz, 1H), 8.01 (dd, J8.6, 1.8 Hz, 1H), 8.40 (d,
J1.8 Hz, 1H). 13C NMR (CDCl3) d 26.6, 55.4, 105.7,
119.7, 124.7, 127.1, 127.8, 130.1, 131.1, 132.6, 137.3,
159.7, 197.9.
6. Gunnewegh, E. A.; Gopie, S. S.; van Bekkum, H. J. Mol. Cat. A
1996, 106, 151±158.
7. Kawada, A.; Mitamura, S.; Kobayashi, S. J. Chem. Soc., Chem.
Commun. 1993, 1157±1158.
8. Kawada, A.; Mitamura, S.; Kobayashi, S. Synlett 1994, 545±
546.
9. (a) Hachiya, I.; Moriwaki, M.; Kobayashi, S. Tetrahedron Lett.
1995, 36, 409±412. (b) Hachiya, I.; Moriwaki, M.; Kobayashi, S.
Bull. Chem. Soc. Jpn 1995, 68, 2053±2060. (c) Kobayashi, S.;
Iwamoto, S. Tetrahedron Lett. 1998, 39, 4697±4700.
10. (a) Kawada, A.; Mitamura, S.; Kobayashi, S. J. Chem. Soc.,
Chem. Commun. 1996, 183±184. (b) Mukaiyama, T.; Suzuki, K.;
Han, J. S.; Kobayashi, S. Chem. Lett. 1992, 435±438.
11. (a) Winstein, S.; Smith, S.; Darwish, D. J. Am. Chem. Soc.
1959, 81, 5511±5512. (b) Pocker, Y.; Buchholz, R. F. J. Am.
Chem. Soc. 1970, 92, 2075±2084. (c) Grieco, P. A.; Nunes, R. J.;
Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595±4596.
12. We have recently found that Sb(OTf)3 was an excellent cata-
lyst for Friedel±Crafts acylation. Kobayashi, S.; Komoto, I.
Unpublished results.
1-Acetyl-2-methoxynaphthalene. A pale yellow crystal.
Mp 54.5±56.58C (lit.16 57±588C). 1H NMR (CDCl3) d
2.65 (s, 3H), 3.98 (s, 3H), 7.29 (d, J9.2 Hz, 1H), 7.37
(ddd, J8.1, 6.9, 1.2 Hz, 1H), 7.48 (ddd, J8.1, 6.9,
1.5 Hz, 1H), 7.76 (d, J8.1 Hz, 1H), 7.80 (d, J8.1 Hz,
1H), 7.89 (d, J9.2 Hz, 1H). 13C NMR (CDCl3) d 32.7,
56.4, 112.8, 123.6, 124.1, 125.1, 127.7, 128.1, 128.8,
130.3, 131.4, 153.9, 205.2.
Acknowledgements
This work was partially supported by CREST, Japan
Science and Technology Corporation (JST), and a Grant-
in-Aid for Scienti®c Research from the Ministry of Educa-
tion, Science, Sports and Culture, Japan.
13. Matsuo, J.; Odashima, K.; Kobayashi, S. Synlett 2000, 403±
405.
14. It was also con®rmed that migration from isolated 1 to 2
occurred under the reaction conditions, while no migration was
observed from isolated 2 to 1 under the same reaction conditions.
Á
15. Labrouillere, M.; Le Roux, C.; Gaspard, H.; Laporterie, A.;
References
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