A Novel and Efficient Synthesisof Camphorquinone from Camphoric Acid

Abstract

Camphorquinone (1), an important finechemical and medicinal product derived from camphor, was efficientlysynthesized from easily available camphoric acid (2).The key steps include acyloin condensation using Me₃SiClas a scavenger of alkoxides and oxidation of the bis(trimethylsilyl)derivative 4 by bromine in CCl₄.The new method offers an efficient alternative synthesis of camphorquinone(1).

Key words

camphor - camphorquinone - cyclization - condensation

References

• 1 Linden LA. In Radiation Curing in Polymer Science and Technology,IV   Fouassier J. Rabek JF. Elsevier AppliedScience; London: 1993.  p.382-398  
• 2 Munksguard EC. Iire M. Asmunssen E. J.Dent. Res.  1986,  64:  1409 
• 3 Park YJ. Chae KH. Rawls HR. Dent.Mat.  1999,  15:  120 
• 4 Bornner MP. Thornton ER. J. Am. Chem. Soc.  1991,  113:  1299 
• 5 Ellis MK. Golding BT. Maude AB. Watson WP. J. Chem.Soc., Perkin. Trans. 1  1991,  747 
• 6 Evans WC. Ridgion JM. Simonsen JL. J. Chem. Soc.  1934,  137 
• 7 Barton DHR. Hui RAHF. Lester DJ. Ley SV. TetrahedronLett.  1979,  20:  3331 
• 8 Hattori K. Yoshida T. Rikuta K. Miyakoshi T. Chem. Lett.  1994,  1885 
• 9 Vedejs E. Engler DA. Telschow JE. J. Org. Chem.  1978,  43:  188 
• 10 Chaussin R. Leriverend P. Pacquer P. J.Chem. Soc., Chem. Commun.  1978,  1032 
• 11 Barton DHR. Cussans NJ. Ley SV. J. Chem. Soc., Chem. Commun.  1978,  393 
• 12 Okada K. Mukai T. Tetrahedron Lett.  1980,  21:  359 
• 13 Creary X. J.Org. Chem.  1980,  45:  2419 
• 14 Burgstahler AW. Boger DL. Naik NC. Tetrahedron  1976,  32:  309 
• 15 Herzog H. Scharf HD. Synthesis  1986,  788 
• 16 Langlois N. Langlois Y. Chiaroni A. Riche C. Tetrahedron Lett.  1989,  30:  1395 
• 17 Hazardsin the Chemical Laboratory   Luxon SG. Royal Society of Chemistry; Cambridge: 1992.  5thed.. p.567 
• 18 Manufacture JRB. inventors; French Patent  1511610.  ; Chem. Abstr. 1969, 70, 68569
• 19 Aishin O. Yasuzo O. Minoru I. Chem.High Polym.  1950,  7:  365 ; Chem. Abstr. 1953, 47, 3822
• 20a Bloomfield JJ. Owsley DC. Nelke JM. Org.React.  1976,  23:  259 
• 20b Finley KT. Chem. Rev.  1964,  64:  573 
• 21 Rühlmann K. Synthesis  1971,  236 
• 22a Bloomfield JJ. Tetrahedron Lett.  1968,  587 
• 22b Bloomfield JJ. Tetrahderon Lett.  1968,  591 
• 23a Philip B. Jeung HS. Synth.Commun.  1986,  16:  775 
• 23b Hiroshi YN. Prabhakar R. Masato T. Chem. Lett.  1993,  315 
• 23c Rasmussen JK. Krepski LR. Heilmann SM. Smith HKII. Tumey ML. Synthesis  1983,  457 
• 23d Tanaka M, and Yamashita H. inventors; Japanese Patent  05202077.  ; Chem. Abstr. 1994, 120, 246099
• 24 Fuschler HM. Heine HG. Hartmann W. Tetrahedron Lett.  1972,  860 
• 25 Strating J. Reiffers S. Wynberg H. Synthesis  1971,  211