Chemoselective and efficient carbomethoxylation of the alcoholic chain of phenols by dimethyl carbonate (DMC)

Tetrahedron Letters

Volumn 48, Issue 39, 2007, Pages 7000-7003

  Bernini, Roberta ^a,b   Mincione, Enrico ^a,b   Crisante, Fernanda ^a,b   Barontini, Maurizio ^a,b   Fabrizi, Giancarlo ^c   Gentili, Patrizia ^c  

^a UNIVERSITY OF TUSCIA   (Italy)

^b Unita di Ricerca VT2   (Italy)

^c SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Carboxymethylated hydroxytyrosol; Chemoselective carbomethoxylation; Dimethyl carbonate (DMC)

Indexed keywords

1,8 DIAZABICYCLO[5.4.0]UNDEC 7 ENE; ALKANOL; CARBONIC ACID; DIMETHYL CARBONIC ACID; HYDROXYTYROSOL; PHENOL; SULFURIC ACID; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ESTERIFICATION; HYDROLYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 34548324457     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.109     Document Type: Article

References (51)

1. For comprehensive reviews on organic carbonates, see:. Shaikh A.-A.G., and Sivaram S. Chem. Rev. 96 (1996) 951-976
2. Parrish J.P., Salvatore R.N., and Jung K.W. Tetrahedron 56 (2000) 8207-8237
3. Deshpande M.M., Jadhav A.S., Gunari A.A., Sehra J.C., and Sivaram S. J. Polym. Sci. 38 (1995) 701-705
4. Pokharkar V., and Sivaram S. Polymer 36 (1995) 4851-4854
5. Bishit K.S., Svirkin Y.Y., Henderson L.A., Gross R.A., Kaplan D.L., and Swift G. Macromolecules 30 (1997) 7735-7742
6. Al-Azemi T.F., and Bishit K.S. Macromolecules 32 (1999) 6536-6540
7. Hardies, D. E.; Rinehart, J. K. US Patent 4 022 609, 1970.
8. Adams, J. B. PCT Int. Appl. WO 04 318, 1992.
9. Avramova P., Dryanovska L., and Ilarionov Y. Pharmazie 32 (1977) 201-206
10. Avramova P., Dryanovska L., and Ilarionov Y. Pharmazie 38 (1983) 443-446
11. Kole H.K., Akamatsu M., ye B., Yan X., Barfortd D., Roller P.P., and Burke T.R. Biochem. Biophys. Res. Commun. 209 (1995) 817-822
12. Ghiron C., Rossi T., and Thomas R.J. Tetrahedron Lett. 38 (1997) 3569-3572
13. Greene T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis (1999), Wiley, New York 179-186
14. Rivetti F. In: Tundo P., and Anastas P. (Eds). Dimethyl Carbonate: An Answer to the Need for Safe Chemical. In Green Chemistry: Challenging Perspectives (2000), Oxford University Press, Oxford 201-219
15. See for example:. Memoli S., Selva M., and Tundo P. Chemosphere 43 (2001) 115-121
16. Tundo P. Pure Appl. Chem. 73 (2001) 117-124
17. Tundo P., and Selva M. Acc. Chem. Res. 35 (2002) 706-716
18. Tundo P., Memoli S., Herault D., and Hill K. Green Chem. 6 (2004) 609-612
19. Tundo P., Rossi L., and Loris A. J. Org. Chem. 70 (2005) 2219-2224
20. Bonino F., Damin A., Bordiga S., Selva M., Tundo P., and Zecchina A. Angew. Chem., Int. Ed. 44 (2005) 4774-4777
21. Shieh W.-C., Dell S., and Repic O. Org. Lett. 3 (2001) 4279-4281
22. Shieh W.-C., Dell S., and Repic O. J. Org. Chem. 67 (2002) 2188-2191
23. Shieh W.-C., Dell S., and Repic O. Tetrahedron Lett. 43 (2002) 5607-5609
24. Kirunakki S.R., Nagaraju N., Murthy K.V.V.S.B.S.R., and Narayanan S. Appl. Cat. A-Gen. 226 (2002) 175-182
25. Zheng Y., Li J., Zhao N., Wei W., and Sun Y. Micropor. Mesopor. Mater. 92 (2006) 195-200
26. Selva M., Tundo P., and Perosa A. J. Org. Chem. 68 (2003) 7374-7378
27. Selva T., and Tundo P. J. Org. Chem. 71 (2006) 1464-1470
28. Breton G.W. J. Org. Chem. 62 (1997) 8952-8954
29. Sabitha G., Reddy B.V.S., Reddy G.S.K.K., and Yadav J.S. New J. Chem. 24 (2000) 63-64
30. Biswanatha D., Venkataiah B., and Madhusudhan P. Synth. Commun. 32 (2002) 249-252
31. 5 (226.23): C, 58.40; H, 6.24; O, 35.36. Found: C, 58.30; H, 6.28; O, 35.42.
32. Ryan D., Antolovich M., Prenzler P., Robards K., and Lavee S. Sci. Hortic. 92 (2002) 147-176
33. De La Fuente P., Chamorro P., Moreno M., and Poza M.A. Inn. Food Tech. 26 (2005) 76-79
34. De La Fuente P., Chamorro P., Moreno M., and Poza M.A. Alimentaria 368 (2005) 134-139
35. Montedoro G., Servili M., Baldioli M., and Miniati E. J. Agric. Food Chem. 40 (1992) 1571-1576
36. Montedoro G., Servili M., Baldioli M., and Miniati E.E. J. Agric. Food Chem. 40 (1992) 1577-1580
37. Manna C., Della Ragione F., Cucciola V., Borriello A., D'Angelo S., Galletti P., and Zappia V. Adv. Exp. Med. Biol. 472 (1999) 115-130
38. Capasso R., Evidente A., Avolio S., and Solla F. J. Agric. Food Chem. 47 (1999) 1745-1748
39. Ferdinando-Bolanos J., Rodriguez G., Rodriguez R., Heredia A., Guillen R., and Jimenez A. J. Agric. Food Chem. 50 (2002) 6804-6811
40. Allouche N., Fki I., and Sayadi S. J. Agric. Food Chem. 52 (2004) 267-273
41. Visioli F., and Galli C. J. Agric. Food Chem. 46 (1998) 4292-4296
42. Hamdi, H. K.; Tavis, J. H.; Castellon, R. WO 02/094193, 2002.
43. Crea, R. WO 03/068171, 2003.
44. Geerlings, A.; Lopez-Huertas, L. E.; Morales Sanchez, J. C.; Boza Puerta, J.; Jimenez Lopez, J. US 02225160, 2003.
45. Dziabo, A. J.; De Brujin, C.; Christ, F. R.; Vigh, J. WO 03/086442, 2003.
46. Geerling, A.; Lopez-Huertas Leon, E.; Morales Sanchez, J. C.; Boza Puerta, J. WO 082798, 2003.
47. Crea, R. US 0039066, 2004.
48. De la Cruz Cortes, J. P.; Gonzalez Correa, J. A.; Sanchez De La Cuesta y Alarcon, F. WO 114467, 2006.
49. Brand-Williams W., Cuvelier M.E., and Berset C. Lebensm.-Wiss. Technol. 28 (1995) 25-30
50. 50, mol/L antioxidant/mol/L DPPH) was extrapolated.
51. Tuck K.L., Hayball P.J., and Stupans I. J. Agric. Food Chem. 50 (2002) 2404-2409