Abstract
4-Nitro-o-xylene was selectively oxidized to 2-methyl-4-nitrobenzoic acid using dilute nitric acid as the oxidizing agent under atmospheric pressure. The oxidation of 4-nitro-o-xylene was effectively promoted by an addition of radical initiators. Under reflux, 2-methyl-4-nitrobenzoic acid was afforded in high yield using nitric acid combined with N-hydroxyphthalimide, cobalt dichloride (CoCl2 · 6H2O), manganese acetate (Mn(OAc)2 · 4H2O) and phase transfer catalyst
References
Bold, G., Caravatti, G., Floersheimer, A., Guagnano, V., Imbach, P., Masuya, K., Roesel, J., Vaupel, A., & Garcia- Echeverria, C. (2005). U.S. patent WO 2005051366A2. Washington, D.C., USA: US Patent and Trademark Office.Suche in Google Scholar
Chupak, L. S., Kaneko, T., Josyula, V. P. V. N., & Jiao, W. (2004). U.S. patent WO 2004069245A1. Washington, D.C., USA: US Patent and Trademark Office.Suche in Google Scholar
Chakrabartty, S. K., & Kretschmer, H. O. (1974). Sodium hypochlorite as a selective oxidant for organic compounds. Journal of the Chemical Society, Perkin Transactions 1, 1974, 222-228. DOI: 10.1039/p19740000222.Suche in Google Scholar
Gerspacher, M., Furet, P., Pissot-Soldermann, C., Gaul, C., Holzer, P., Vangrevelinghe, E., Lang, M., Erdmann, D., Radimerski, T., Regnier, C. H., Chene, P., De Pover, A., Hofmann, F., Baffert, F., Buhl, T., Aichholz, R., Blasco, F., Endres, R., Trappe, J., & Drueckes, P. (2010). 2-Amino-aryl-7-aryl-benzoxazoles as potent, selective and orally available JAK2 inhibitors. Bioorganic & Medicinal Chemistry Letters, 20, 1724-1727. DOI: 10.1016/j.bmcl.2010.01.069.Suche in Google Scholar
Huntress, E. H., Shloss, E. L., Jr., & Ehrlich, P. (1936). 4- Nitrophthalic acid. Organic Syntheses, 16, 56. DOI: 10.15227 /orgsyn.016.0056.Suche in Google Scholar
Yavari, I., & Karimi, E. (2009). N-Hydroxyphthalimide-catalyzed oxidative production of phthalic acid from xylenes using O2/HNO3 in an ionic liquid. Synthetic Communications, 39, 3420-3427. DOI: 10.1080/00397910902770461.Suche in Google Scholar
Ishii, Y., Nakayama, K., Takeno, M., Sakaguchi, S., Iwahama, T., & Nishiyama, Y. (1995). Novel catalysis of Nhydroxyphthalimide in the oxidation of organic substrates by molecular oxygen. Journal of Organic Chemistry, 60, 3934-3935. DOI: 10.1021/jo00118a002.Suche in Google Scholar
Liu, G. Y., Tang, R. R., & Wan, Z. (2014). Metal-free allylic oxidation with molecular oxygen catalyzed by g-C3N4 and N-hydroxyphthalimide. Catalysis Letters, 144, 717-722. DOI: 10.1007/s10562-014-1200-1.Suche in Google Scholar
Mahindroo, N., Punchihewa, C., Bail, A. M., & Fujii, N. (2008). Indole-2-amide based biochemical antagonist of Dishevelled PDZ domain interaction down-regulates Dishevelled-driven Tcf transcriptional activity. Bioorganic & Medicinal Chemistry Letters, 18, 946-949. DOI: 10.1016/j.bmcl.2007.12.039.Suche in Google Scholar
Recupero, F., & Punta, C. (2007). Free radical functionalization of organic compounds catalyzed by N-hydroxyphthalimide. Chemical Reviews, 107, 3800-3842. DOI: 10.1021/cr040170k.Suche in Google Scholar
Sawatari, N., Sakaguchi, S., & Ishii, Y. (2003). Oxidation of nitrotoluenes with air using N-hydroxyphthalimide analogues as key catalysts. Tetrahedron Letters, 44, 2053-2056. DOI: 10.1016/s0040-4039(03)00212-0.Suche in Google Scholar
Sasson, Y., Zappi, D. G., & Neumann, R. (1986). Liquidphase oxidation of deactivated methylbenzenes by aqueous sodium hypochlorite catalyzed by ruthenium salts under phase-transfer catalytic conditions. Journal of Organic Chemistry, 51, 2880-2883. DOI: 10.1021/jo00365a005.Suche in Google Scholar
Taha, N., Chidambaram, M., Dakka, J., & Sasson, Y. (2009). Co(II) catalyzed solvent free auto-oxidation of methylbenzenes to substituted benzoic acids under phase transfer conditions. Catalysis Letters, 129, 358-362. DOI: 10.1007/s10562-009-9874-5.Suche in Google Scholar
Taha, N., & Sasson, Y. (2010). Superior performance of NHPI co-catalyst in the autoxidation of methylbenzenes under solvent-free phase transfer conditions. Organic Process Research & Development, 14, 701-704. DOI: 10.1021/op100 027s.Suche in Google Scholar
Tashiro, Y., Iwahama, T., Sakaguchi, S., & Ishii, Y. (2001). A new strategy for the preparation of terephthalic acid by the aerobic oxidation of p-xylene using N-hydroxyphthalimide as a catalyst. Advanced Synthesis & Catalysis, 343, 220-225. DOI: 10.1002/1615-4169(20010226)343:2<220::AIDADSC220> 3.0.CO;2-N.Suche in Google Scholar
Tsantrizos, Y. S., Chabot, C., Beaulieu, P., Brochu, C., Poirier, M., Stammers, T. A., Thavonekham, B., & Rancourt, J. (2005). U.S. patent WO 2005080388A1. Washington, D.C., USA: US Patent and Trademark Office.Suche in Google Scholar
Zahalka, A. H., & Sasson, Y. (1984). Deactivation of anion phase transfer catalysis by hydrogen bonding extraction acidic compounds. Journal of the Chemical Society, Chemical Communications, 1984, 1581-1582. DOI: 10.1039/c39840001581.Suche in Google Scholar
Zhang, X., Zhou, X. L., Kisliuk, R. L., Piraino, J., Cody, V., & Gangjee, A. (2011). Design, synthesis, biological evaluation and X-ray crystal structure of novel classical 6,5,6-tricyclic benzo[4,5]thieno[2,3-d]pyrimidines as dual thymidylate synthase and dihydrofolate reductase inhibitors. Bioorganic & Medicinal Chemistry, 19, 3585-3594. DOI: 10.1016/j.bmc.2011.03.067. Suche in Google Scholar
© 2015 Institute of Chemistry, Slovak Academy of Sciences
Artikel in diesem Heft
- Liquid–liquid extraction and cloud point extraction for spectrophotometric determination of vanadium using 4-(2-pyridylazo)resorcinol
- Sensitive and selective determination of peptides, PG and PGP, using a novel fluorogenic reagent 4-chlorobenzene-1,2-diol
- Spectroscopy studies of sandwich-type complex of silver(I) co-ordinated to nuclear fast red and adenine and its analytical applications
- Differentiation of selected blue writing inks by surface-enhanced Raman spectroscopy
- A simple pyridine-based colorimetric chemosensor for highly sensitive and selective mercury(II) detection with the naked eye
- Phospho sulfonic acid as efficient heterogeneous Brønsted acidic catalyst for one-pot synthesis of 14H-dibenzo[a,j ]xanthenes and 1,8-dioxo-octahydro-xanthenes
- Microfiltration of post-fermentation broth with backflushing membrane cleaning
- Mass transfer examination in electrodialysis using limiting current measurements
- Determination of diffusivity from mass transfer measurements in a batch dialyzer: numerical analysis of pseudo-steady state approximation
- Structural and thermal characterization of copper(II) complexes with phenyl-2-pyridylketoxime and deposition of thin films by spin coating
- Oxidation of 4-nitro-o-xylene with nitric acid using N-hydroxyphthalimide under phase transfer conditions
- Synthesis of pyranopyrazoles, benzopyrans, amino-2-chromenes and dihydropyrano[c]chromenes using ionic liquid with dual Brønsted acidic and Lewis basic sites
- Eco-friendly conjugate hydrocyanation of α-cyanoacrylates using potassium hexacyanoferrate(II) as cyanating reagent
- Morphological orders of spherulitic crystal textures in Belousov–Zhabotinsky-type oscillatory reaction system
- Zwitterionic structures of selenocysteine-containing dipeptides and their interactions with Cu(II) ions
Artikel in diesem Heft
- Liquid–liquid extraction and cloud point extraction for spectrophotometric determination of vanadium using 4-(2-pyridylazo)resorcinol
- Sensitive and selective determination of peptides, PG and PGP, using a novel fluorogenic reagent 4-chlorobenzene-1,2-diol
- Spectroscopy studies of sandwich-type complex of silver(I) co-ordinated to nuclear fast red and adenine and its analytical applications
- Differentiation of selected blue writing inks by surface-enhanced Raman spectroscopy
- A simple pyridine-based colorimetric chemosensor for highly sensitive and selective mercury(II) detection with the naked eye
- Phospho sulfonic acid as efficient heterogeneous Brønsted acidic catalyst for one-pot synthesis of 14H-dibenzo[a,j ]xanthenes and 1,8-dioxo-octahydro-xanthenes
- Microfiltration of post-fermentation broth with backflushing membrane cleaning
- Mass transfer examination in electrodialysis using limiting current measurements
- Determination of diffusivity from mass transfer measurements in a batch dialyzer: numerical analysis of pseudo-steady state approximation
- Structural and thermal characterization of copper(II) complexes with phenyl-2-pyridylketoxime and deposition of thin films by spin coating
- Oxidation of 4-nitro-o-xylene with nitric acid using N-hydroxyphthalimide under phase transfer conditions
- Synthesis of pyranopyrazoles, benzopyrans, amino-2-chromenes and dihydropyrano[c]chromenes using ionic liquid with dual Brønsted acidic and Lewis basic sites
- Eco-friendly conjugate hydrocyanation of α-cyanoacrylates using potassium hexacyanoferrate(II) as cyanating reagent
- Morphological orders of spherulitic crystal textures in Belousov–Zhabotinsky-type oscillatory reaction system
- Zwitterionic structures of selenocysteine-containing dipeptides and their interactions with Cu(II) ions