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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 3
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Original Articles

Mild and Reversible Friedel-Crafts Acylation: Synthesis of 6-Acyl-2-methoxynaphthalenes

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Pages 383-392 | Received 25 Sep 1989, Published online: 24 Oct 2006

References

  • Pearson , D. E. and Buehler , C. A. 1971 . Synthesis , : 455 For a Review see
  • Agranat , I. , Shih , Y.-S. and Bentor , Y. 1974 . J.Am. Chem. Soc. , 96 : 1259 ibid., 1977, 99, 7068, Olah, G. A., Laali, K., Mehrotra, A. K. J. Org. Chem., 1983, 48, 3360.
  • Giordano , C. , Castaldi , G. and Uggeri , F. 1984 . Angew. Chem. , 96 : 4113 Angew. Chem. Int. Ed. Engl., 1984, 23, 413, Giordano, C., Castaldi, G., Cavic-chioli, S., Villa, M. Tetrahedron, 1989, 45, 4243, Castaldi, G., Cavicchioli, S., Giordano, C., Uggeri, F. J. Org. Chem., 1987, 52, 3018, ibid, 1987, 52, 5642, Tsuchihashi, G. Tetrahedron Lett., 1982, 23, 5427.
  • Rahway , V. 1983 . 10th Ed. 920 The Merck Index, Merck & Co., Inc. . Scrip World Pharm. News, 1986, 26, 12.
  • Seligman , A. M. and Rutenburg , A. M. 1950 . J.Am. Chem. Soc. , 72 : 3214 (b) Buu-Hoï, NG. PM. Rec. Trav. Chim., 1949, 68, 759, (c) Girdler, R. B., Gore, P. H., Hoskins, J. A. J. Chem. Soc.(C), 1966, 181, (d) Horeau, A., Jacques, J. Bull. Soc. Chim.Fr., 1954, 511. (e) Arsenijevic, L., Arsenijevic, V., Horeau, A., Jacques, J. Org. Syntheses, Coll. VI, 34.
  • The method, scaled up for the industrial production, provides 3a in 85% yield, based on converted 1.
  • 7-Acyl-2-methoxynaphthalenes, kinetically disfavoured for electronic reasons, are expected to be at least as stable as the 6-isomers.
  • Rapala , T. R. , Bryan , W. R. , Truett , W. L. and Johnson , W. S. 1962 . J. Org. Chem. , 27 : 3814
  • Chadwick , D. H. and Fuson , R. C. 1948 . J. Org. Chem. , 13 : 484
  • Shilow , E. A. and Burmistrow , S. I. 1947 . Z. Obsch. Chim. , 17 : 1684 Chem. Abstr., 1948, 42, 2595.
  • Salman , R. S. 1985 . Mag. Res. Chem. , 23 : 2 119

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