Metody syntezy witaminy K3

• Autorzy: Kowalski Jan , Płoszyńska Jolanta , Sobkowiak Andrzej

Warianty tytułu

EN

The methods of vitamin K3 synthesis

• Języki publikacji: PL

Abstrakty

EN

The preparation of 2-methyl-1,4naphthoquinone (menadione) is a challenging problem in catalysis research. This reaction is the key step in the synthesis of vitamin K and its derivatives. The preparation of naphthoquinones usually requires the direct oxidation of arenes by stoichiometric quantities of chromic acid/sulfuric acid. The reaction can be also achieved by the use of Ce(IV) compounds and other transition metal compounds as oxidants and with hydrogen peroxide. The other approach is to use Diels-Alder reaction between 1,3-butadiene and p-benzoquinone with the subsequent oxidation of the adduct formed . The indirect electrolysis with ruthenium compounds and dichromate as mediators were also applied in the process. In the previous work we reported that the electrochemical oxidation of 2-methylnaphthalene in glacial acetic acid gives monoacetates, mainly 2-methylnaphthalene-1-acetate, but 2-methylnaphthalene-1,4-diacetate and 2-methyl-1,4-naphthoquinone were also formed. This prompted us to investigate the electrochemical behavior of 2-methylnaphthalene-1,4diacetate. It is shown that the electrochemical oxidation of the compounds in glacial acetic acid yields 2-methyl-1,4naphthoquinone as a sole product. The process is irreversible and diffusion controlled. The material and current yields of the process are 94 and 99% respectively.

Słowa kluczowe

PL

witamina K3; menadion; naftochinon; utlenianie; elektrochemia; synteza organiczna

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 1999
• Tom: [Z] 53, 5-6
• Strony: 401--413
• Opis fizyczny: schem., bibliogr. 39 poz.

Twórcy

autor

Kowalski Jan

• Katedra Chemii Ogólnej i Elektrochemii, Wydział Chemiczny, Politechnika Rzeszowska skr. poczt. 85, 35-959 Rzeszów

autor

Płoszyńska Jolanta

• Katedra Chemii Ogólnej i Elektrochemii, Wydział Chemiczny, Politechnika Rzeszowska skr. poczt. 85, 35-959 Rzeszów

autor

Sobkowiak Andrzej

• Katedra Chemii Ogólnej i Elektrochemii, Wydział Chemiczny, Politechnika Rzeszowska skr. poczt. 85, 35-959 Rzeszów

• Katedra Chemii Ogólnej i Elektrochemii, Wydział Chemiczny. Politechnika Rzeszowska. skr.poczt. 85 35-959 Rzeszów

Bibliografia

• [1] P. Dowd, R. Hershline, S. W. Ham, S. Naganathan, Science, 1995, 269, 1684.
• [2] J. W. Sut tie, The Fat-soluble Vitamins, H. F. DeLuca Ed., Chapter 4 „Vitamin K”, Plenum Press, London 1978.
• [3] Houben-Weyl Methoden der organischen Chemie, 4 Aufl. Band VII/2a, „Chinone”, Teil 1, Georg Thieme Verlag, Stuttgart 1977, s. 23.
• [4] M. Hudlicky, Oxidations in Organic Chemistry, ACS Monograph 186, American Chemical Society, Washington 1990, s. 94.
• [5] R. A. Sheldon, J. K. Koch i, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York 1981, s. 257.
• [6] S. Chocron, M. Michman, Appl. Catal., 1990, 62, 119.
• [7] M. Periasamy, M. V. Bhatt, Tetrahedron Lett., 1978, 4561.
• [8] T. L. Ho, Synthesis, 1973, 347.
• [9] Houben-Weyl Methoden der organischen Chemie, 4 Aufl., Band IV/lb, „Oxidation”, Teil 2, Georg Thieme Verlag, Stuttgart 1973, s. 153.
• [10] V. Steglinska, A. Gzheidzyak, Y. Dzegets, Zh. Obshch. Khim., 1996, 66, 847.
• [11] J. Skarżewski, Tetrahedron, 1984, 40, 4997.
• [12] S. Naganathan, R. Hershline, S. W. Ham, P. Dowd, J. Am. Chem. Soc., 1994,116, 9831.
• [13] S. Yamaguchi, M. Inone, S. Enomoto, Chem. Lett., 1985, 827.
• [14] W. Adam, W. A. Herrmann, J. Lin, C. R. Saha-Moller, R. W. Fischer, J. D. G. Correia, Angew. Chem. Int. Ed. Engl., 1994, 33, 2475.
• [15] Z. Song, A. Sorokin, J. Bernadou, B. Meunier, J. Org. Chem., 1997, 62, 673.
• [16] K. I. Matveev, E. G. Zhizhina, V. F. Odyakov, V. N. Parmon, Izv. Akad. Nauk, Ser. Khim., 1994, 1208.
• [17] K. I. Matveev, E. G. Zhizhina, V. F. Odyakov, React. Kinet. Catal. Lett., 1995, 55, 47.
• [18] K. I. Matveev, E. G. Zhizhina, V. F. Odyakov, N. S. Kotsarenko, V. P. Shmach- kova, React. Kinet. Catal. Lett., 1996, 57, 375.
• [19] Houben-Weyl Methoden der organischen Chemie, 4 Aufl., Band VII/2a, „Chinone”, Teil 1, Georg Thieme Verlag, Stuttgart 1977, s. 80.
• [20] F. Farina, E. Fernandez, V. Gimeno, J. A. Valderrama, Ann. Quim. 1995, 91, 220.
• [21] A. V. Rama Rao, V. H. Deshpande, K. Ravichandran, Indian J. Chem., 1985, 24B, 233.
• [22] J. D. Genders, D. Pletcher, Chem. Ind., 1996, 682.
• [23] New Challenges in Organie Electrochemistry, T. Osa Ed, Gordon and Breach Science Publishers, Amsterdam 1998.
• [24] E. Steckhan, Top. Curr. Chem., 1987, 142, 1.
• [25] S. Chocron, M. Michman, J. Mol. Catal., 1991, 66, 85.
• [26] S. Chocron, M. Michman, Appi. Catal., 1993, 83, 251.
• [27] R. P. Krah, R. M. Spotnitz, J. T. Lundquist, J. Org. Chem., 1989, 54, 1526.
• [28] N. L. Weinberg, w: Technique of Electroorganic Synthesis, N. L. Weinberg Ed, Wiley, New York 1974, s. 252.
• [29] L. Eberson, K. Nyberg, J. Am. Chem. Soc., 1966, 88, 1686.
• [30] L. Eberson, ibid., 1967, 89, 4669.
• [31] V. M. Clark, M. R. Eraut, D. W. Hutchinson, J. Chem. Soc. (C), 1969, 79.
• [32] V. D. Parker, J. Chem. Soc., Chem. Commun., 1969, 610.
• [33] E. P. Meier, J. Q. Chambers, J. Electroanal. Chem., 1970, 25, 435.
• [34] J. Kowalski, J. Ploszynska, Electrochim. Acta, 1990, 35, 1739.
• [35] J. March, Advanced Organic Chemistry, 4th ed. Wiley, New York 1992, s. 515 i literatura tam cytowana.
• [36] R. W. Aider, R. Baker, J. M. Brown, Mechanizmy reakcji w chemii organicznej, PWN, Warszawa 1977, s. 267.
• [37] C. Eaborn, P. Folborn, R. E. Spillett, R. Taylor, J. Chem. Soc. (B), 1968, 1112.
• [38] J. Kowalski, J. Ploszynska, A. Sobkowiak, J. Appl. Electrochem., 1998, 28, 1261.
• [39] Houben-Weyl Methoden der organischen Chemie, 4. Aufl., Band II, „Analytische Methoden”, Georg Thieme Verlag, Stuttgart 1953, s. 510.