Hafnium trifluoromethanesulfonate (Hf(OTf)4) as an efficient catalyst in the Fries rearrangement and direct acylation of phenol and naphthol derivatives

Tetrahedron Letters

Volumn 37, Issue 12, 1996, Pages 2053-2056

  Kobayashi, Shü ^a   Moriwaki, Mitsuhiro ^a   Hachiya, Iwao ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029914517     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00216-X     Document Type: Article

References (26)

1. Crouse, D. J.; Hurlbut, S. L.; Wheeler, M. S. J. Org. Chem. 1981, 46, 374.
2. (a) Takanishi, Y.; Ouchi, Y.; Takezoe, H.; Fukuda, A.; Mochizuki, A.; Nakatsuka, M. Mol. Cryst. Liq. Cryst. 1991, 199, 111.
3. (b) Mochizuki, A.; Kobayashi, S. ibid. 1994, 243, 77.
4. Martin, R. Org. Prep. Proced. Int. 1992, 24 , 369.
5. (a) Niyazov, A. N.; Namatov, B.; Atlyev, Kh. Izv. Akad. Nauk Turkn. SSR, Ser. Fiz.-Tekh., Khim. Geol. Nauk 1974, (4), 62; CA 1975, 82, 170275d.
6. (a) Niyazov, A. N.; Namatov, B.; Atlyev, Kh. Izv. Akad. Nauk Turkn. SSR, Ser. Fiz.-Tekh., Khim. Geol. Nauk 1974, (4), 62; CA 1975, 82, 170275d.
7. (b) Niyazov, A. N.; Namatov, B.; Atlyev, Kh. Izv. Akad. Nauk Turkn. SSR, Ser. Fiz.-Tekh., Khim. Geol. Nauk 1974, (6), 65; CA 1975, 83, 58366d.
8. (b) Niyazov, A. N.; Namatov, B.; Atlyev, Kh. Izv. Akad. Nauk Turkn. SSR, Ser. Fiz.-Tekh., Khim. Geol. Nauk 1974, (6), 65; CA 1975, 83, 58366d.
9. (c) Namatov, B.; Atlyev, Kh. Mater. Resp. Nauchno-Tekh. Konf. Molodykh Uch. Pererab. Nefti Neftekhim., 2nd 1974, 166; CA 1976, 85, 77796b.
10. (c) Namatov, B.; Atlyev, Kh. Mater. Resp. Nauchno-Tekh. Konf. Molodykh Uch. Pererab. Nefti Neftekhim., 2nd 1974, 166; CA 1976, 85, 77796b.
11. (d) Trost, B. M.; Saulnier, M. G. Tetrahedron Lett. 1985, 26, 123.
12. (e) Crombie, L.; Jones, R. C. F.; Palmer, C. J. ibid. 1985, 26, 2933.
13. (a) Dorofeenko, G. N.; Tkachenko, V. V. Khim. Geterotsikl. Soedin. 1971, 7 (12), 1703; CA 1972, 76, 153503k.
14. (a) Dorofeenko, G. N.; Tkachenko, V. V. Khim. Geterotsikl. Soedin. 1971, 7 (12), 1703; CA 1972, 76, 153503k.
15. (b) Dorofeenko, G. N.; Tkachenko, V. V. Khim. Geterotsikl. Soedin. 1974, (2), 176; CA 1974, 81, 13347r.
16. (b) Dorofeenko, G. N.; Tkachenko, V. V. Khim. Geterotsikl. Soedin. 1974, (2), 176; CA 1974, 81, 13347r.
17. o-Acylation of phenols via phenol salts under basic conditions has been reported. Sartori G.; Bigi. F. J. Org. Chem. 1990, 55, 4371, and references cited therein.
18. Kobayashi, S.; Moriwaki, M.; Hachiya, I. J. Chem. Soc., Chem. Commun. 1995, 1527.
19. (a) Hachiya, I.; Moriwaki, M.; Kobayashi, S. Tetrahedron Lett. 1995, 36, 409.
20. (b) Hachiya, I.; Moriwaki, M.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1995, 68, 2053.
21. 3, respectively.
22. 4). The solvents were removed under reduced pressure and the crude product was chromatographed on silica gel to afford 2-hydroxy-4-methylphenyl methyl ketone in a 64% yield.
23. For example, (a) Chatterjea, J. N.; Gupta, S. N. P.; Mehrotra, V. N. J. Indian Chem. Soc. 1965, 42, 205.
24. (b) Martin, R.; Betoux, J. M.; Coton, G. Bull. Soc. Chim. Fr. 1972, 4319, and references cited therein.
25. 3 is also effective in the direct acylation. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. Full details including comparison of catalysts will be reported in due course.
26. 4). The solvents were removed under reduced pressure and the crude product was chromatographed on silica gel to afford 2-hydroxy-4-methoxylphenyl methyl ketone in an 84% yield.