From Chemistry Towards Technology Step-By-Step From Chemistry Towards Technology Step-By-Step От химии к технологии шаг за шагом 2782-1900 81530 10.52957/2782-1900-2024-4-2-97-103 Научные статьи Scientific articles Научные статьи Synthesis of substituted 4-aryloxypthalic acids based on 4-nitro-N-methylphthalimide Synthesis of substituted 4-aryloxypthalic acids based on 4-nitro-N-methylphthalimide Бухалин Владимир Владимирович Bukhalin Vladimir Vladimirovich Баклагин Вячеслав Леонидович Baklagin Vyacheslav Leonidovich Котов Александр Дмитриевич Kotov Aleksandr Dmitrievich kotad@mail.ru

доктор технических наук;

doctor of technical sciences;

 Абрамов Игорь Геннадьевич Abramov Igor Gennadevich abramovig@ystu.ru

доктор химических наук;

doctor of chemical sciences;

 Ярославский государственный технический университет Yaroslavl State Technical University Ярославский государственный педагогический университет им. К.Д. Ушинского Yaroslavl State Pedagogical University named after K.D. Ushinsky 23 06 2023 23 06 2023 4 2 97 103 25 05 2023 16 06 2023 https://chemintech.ru/en/nauka/article/81530/view

Based on an activated aromatic nucleophilic substitution reaction between 4-nitro-N-methylphthalimide and phenols containing different substituents we obtained both identified and unidentified 4-aryloxy-N-methylphthalimides. Their alkaline hydrolysis gave 4-aryloxyphthalic acids.

Based on an activated aromatic nucleophilic substitution reaction between 4-nitro-N-methylphthalimide and phenols containing different substituents we obtained both identified and unidentified 4-aryloxy-N-methylphthalimides. Their alkaline hydrolysis gave 4-aryloxyphthalic acids.

 4-nitro-N-methylphthalimide activated aromatic nucleophilic substitution substituted aryloxypthalic acids arylenedioxypthalic acids aryloxy-N-methylphthalimides

Radko, L.V., Ivanova, V.M., Taranova, S.N., Dorogov, M.V., Vulakh, E.L. & Barque, D.S. (1995) Method of preparation of 4-nitro-N-methylphthalimide. RU 2044726 (in Russian). Radko, L.V., Ivanova, V.M., Taranova, S.N., Dorogov, M.V., Vulakh, E.L. & Barque, D.S. (1995) Method of preparation of 4-nitro-N-methylphthalimide. RU 2044726 (in Russian). Rajasekar, S., & Venkatesan, D. (2013) Synthesis and characterization of poly(amideimides)s from 4-(p-carboxyphenoxy)phthalic anhydride and 4-(p-carboxybenzoyl)phthalic anhydride, Polymer, 54 (21), pp. 5626 5633. DOI: 10.1016/j.polymer.2013.08.037. Rajasekar, S., & Venkatesan, D. (2013) Synthesis and characterization of poly(amideimides)s from 4-(p-carboxyphenoxy)phthalic anhydride and 4-(p-carboxybenzoyl)phthalic anhydride, Polymer, 54 (21), pp. 5626 5633. DOI: 10.1016/j.polymer.2013.08.037. Plakhtinsky, V.V, Abramov, I.G., Milto, V.I., Krasovskaya, G.G. & Dobrokhotov O.V. (2012) Method for obtaining 4,4’-(m-phenylenedioxy) diphthalonitrile. RU 2459803 (in Russian). Plakhtinsky, V.V, Abramov, I.G., Milto, V.I., Krasovskaya, G.G. & Dobrokhotov O.V. (2012) Method for obtaining 4,4’-(m-phenylenedioxy) diphthalonitrile. RU 2459803 (in Russian). Botnar, A.A., Domareva, N.P., Kazaryan, K.Y., Tikhomirova, T.V., Abramova, M.B. & Vashurin, A.S. (2022) Synthesis and spectral properties of tetraphenoxysubstituted erbium phthalocyanines containing peripheral phenyl and cyclohexyl fragments, Russian Chemical Bulletin, 71(5), pp. 953-961. DOI: 10.1007/slll72-022-3496-0. Botnar, A.A., Domareva, N.P., Kazaryan, K.Y., Tikhomirova, T.V., Abramova, M.B. & Vashurin, A.S. (2022) Synthesis and spectral properties of tetraphenoxysubstituted erbium phthalocyanines containing peripheral phenyl and cyclohexyl fragments, Russian Chemical Bulletin, 71(5), pp. 953-961. DOI: 10.1007/slll72-022-3496-0. Znoiko, S.A., Elizarova, A.P., Kustova, T.V. & Nakonechnaya, A.N. (2021) Complexes of erbium and lutetium of the “sandwich” type, containing fragments of tetraanthraquinonoporphyrazine and substituted phthalocyanines, Izvestiya vuzov. Khimiya i khimicheskaya tekhnologiya, 64(4), pp. 42-51. DOI: 10.6060/ivkkt.20216404.6380 (in Russian). Znoiko, S.A., Elizarova, A.P., Kustova, T.V. & Nakonechnaya, A.N. (2021) Complexes of erbium and lutetium of the “sandwich” type, containing fragments of tetraanthraquinonoporphyrazine and substituted phthalocyanines, Izvestiya vuzov. Khimiya i khimicheskaya tekhnologiya, 64(4), pp. 42-51. DOI: 10.6060/ivkkt.20216404.6380 (in Russian). Orlova, A.M., Alentiev, A.Yu., Kolesnikov, T.I., Tsegelskaya, A.Yu., Monakhova, K.Z., Chirkov, S.V., Nikiforov, R.Yu., Abramov, I.G. & Kuznetsov, A.A. (2022) Novel organo-soluble poly(etherimide)s based on diethyltoluenediamine: Synthesis, characterization and gas transport properties, Polymer, (256), pp. 125258. DOI: https://doi.Org/10.1016/j.polymer.2022.125258. Orlova, A.M., Alentiev, A.Yu., Kolesnikov, T.I., Tsegelskaya, A.Yu., Monakhova, K.Z., Chirkov, S.V., Nikiforov, R.Yu., Abramov, I.G. & Kuznetsov, A.A. (2022) Novel organo-soluble poly(etherimide)s based on diethyltoluenediamine: Synthesis, characterization and gas transport properties, Polymer, (256), pp. 125258. DOI: https://doi.Org/10.1016/j.polymer.2022.125258. Soldatova, A.E., Tsegelskaya, A.Yu., Semenova, G.K., Bezsudnov, I.V., Polinskaya, M.S., Abramov, I.G. & Kuznetsov, A.A. (2022) Synthesis of tetraarm stars with polyetherimide-polyether block copolymer arms, Russian Chemical Bulletin, 71(4), pp. 777-786. DOI: 10.1007/s11172-022-3478-2. Soldatova, A.E., Tsegelskaya, A.Yu., Semenova, G.K., Bezsudnov, I.V., Polinskaya, M.S., Abramov, I.G. & Kuznetsov, A.A. (2022) Synthesis of tetraarm stars with polyetherimide-polyether block copolymer arms, Russian Chemical Bulletin, 71(4), pp. 777-786. DOI: 10.1007/s11172-022-3478-2. Orlova, A.M., Tsegelskaya, A.Yu., Kolesnikov, T.I., Abramov, I.G., Kuznetsov, A.A. (2022) Novel Polyetherimides Based on 5-Methyl-l,3-phenylene-bis-4-oxyphthalic Acid Dianhydride: Synthesis and Physicochemical Properties, Polymer Science, Series B, 64(1), pp. 17-25. DOI: 10.1134/S1560090422010031. Orlova, A.M., Tsegelskaya, A.Yu., Kolesnikov, T.I., Abramov, I.G., Kuznetsov, A.A. (2022) Novel Polyetherimides Based on 5-Methyl-l,3-phenylene-bis-4-oxyphthalic Acid Dianhydride: Synthesis and Physicochemical Properties, Polymer Science, Series B, 64(1), pp. 17-25. DOI: 10.1134/S1560090422010031. Berezin, D.B., Makarov, V.V., Znoyko, S.A., Mayzlish, V.E. & Kustov, A.V. (2020) Aggregation water soluble octaanionicphthalocyanines behavior and their photoinactivation antimicrobial effect in vitro, Mendeleev Communications, 30(5), pp. 621-623. DOI: 10.1016/j.mencom.2020.09.023. Berezin, D.B., Makarov, V.V., Znoyko, S.A., Mayzlish, V.E. & Kustov, A.V. (2020) Aggregation water soluble octaanionicphthalocyanines behavior and their photoinactivation antimicrobial effect in vitro, Mendeleev Communications, 30(5), pp. 621-623. DOI: 10.1016/j.mencom.2020.09.023. Abramov, I.G., Plakhtinsky, V.V., Abramova, M.B., Smirno,v A.V. & Krasovskaya, G.G. (1999) Synthesis of heterylphthalonitriles, Khimiya geterociklicheskih soedinenij, (11), pp. 1537-1539 (in Russian). Abramov, I.G., Plakhtinsky, V.V., Abramova, M.B., Smirno,v A.V. & Krasovskaya, G.G. (1999) Synthesis of heterylphthalonitriles, Khimiya geterociklicheskih soedinenij, (11), pp. 1537-1539 (in Russian). Abramov, I.G., Guseva, V.V., Balagurova, E.V. & Zakharkin, L.I. (1999) The first example of the reaction of nucleophilic substitution of the nitro group in 4-nitrophthalonitrile for carboranyl group under the action of B-derivative of carborane, Zhurnal obshchej khimii, 69(10), pp. 1753 (in Russian). Abramov, I.G., Guseva, V.V., Balagurova, E.V. & Zakharkin, L.I. (1999) The first example of the reaction of nucleophilic substitution of the nitro group in 4-nitrophthalonitrile for carboranyl group under the action of B-derivative of carborane, Zhurnal obshchej khimii, 69(10), pp. 1753 (in Russian). Abramov, I.G., Baklagin, V.L., Makarova, E.S. & Kleykova D.E. (2021) Use of nitrogen-containing heterocyclic O- and S-nucleophiles in reactions with 4-nitrophthalonitrile and 4-bromo-5-nitrophthalonitrile, From Chemistry Towards Technology Step-By-Step, 2(4), pp. 43-49. DOI: 10.52957/2782I900_2021_04_43 [online]. Available at: http://chemintech.ru/index.php/tor/2021-2-4 Abramov, I.G., Baklagin, V.L., Makarova, E.S. & Kleykova D.E. (2021) Use of nitrogen-containing heterocyclic O- and S-nucleophiles in reactions with 4-nitrophthalonitrile and 4-bromo-5-nitrophthalonitrile, From Chemistry Towards Technology Step-By-Step, 2(4), pp. 43-49. DOI: 10.52957/2782I900_2021_04_43 [online]. Available at: http://chemintech.ru/index.php/tor/2021-2-4 Malyasova, A.S., Kostrova, E.A., Abramov, I.G., Maizlish, V.E. & Koifman, O.I. (2021) Synthesis, acid-base interactions, and photostability of copper(II) tetrakis(3,5-di-tert-butylbenzoyloxy)phthalocyanine, Russian Chemical Bulletin, 70(12), pp. 2405-2415. DOI: 10.1007/s11172-021-3360-7. Malyasova, A.S., Kostrova, E.A., Abramov, I.G., Maizlish, V.E. & Koifman, O.I. (2021) Synthesis, acid-base interactions, and photostability of copper(II) tetrakis(3,5-di-tert-butylbenzoyloxy)phthalocyanine, Russian Chemical Bulletin, 70(12), pp. 2405-2415. DOI: 10.1007/s11172-021-3360-7. Milto, V.I., Tarasov, A.V., Nozhnin, N.A., Shlenev, R.M., Svetlichny, V.M. & Yudin, V.E. (2020) Development of laboratory technology for the synthesis of dianhydride R, a monomer for thermoplastic polyetherimides, Novye polimernye kompozicionnye materialy. Mikitaevskie chteniya: sbornik trudov XVI Mezhdunarodnoj nauchno-prakticheskoj konferencii, Nalchik: Izd-vo «Print Centr», pp. 292-295 (in Russian). Milto, V.I., Tarasov, A.V., Nozhnin, N.A., Shlenev, R.M., Svetlichny, V.M. & Yudin, V.E. (2020) Development of laboratory technology for the synthesis of dianhydride R, a monomer for thermoplastic polyetherimides, Novye polimernye kompozicionnye materialy. Mikitaevskie chteniya: sbornik trudov XVI Mezhdunarodnoj nauchno-prakticheskoj konferencii, Nalchik: Izd-vo «Print Centr», pp. 292-295 (in Russian). Milto, V.I., Nozhnin, N.A., Tarasov, A.V. & Rybina, G.V. (2023) Development of an applied method for the synthesis of 4,4’-(m-phenylenedioxy)-N-methylphthalimide, an intermediate for the production of polyetherimides, Izvestiya Kabardino-balkarskogo gosudarstvennogo universiteta, XIII(1), pp. 69-73 (in Russian). Milto, V.I., Nozhnin, N.A., Tarasov, A.V. & Rybina, G.V. (2023) Development of an applied method for the synthesis of 4,4’-(m-phenylenedioxy)-N-methylphthalimide, an intermediate for the production of polyetherimides, Izvestiya Kabardino-balkarskogo gosudarstvennogo universiteta, XIII(1), pp. 69-73 (in Russian). Relles, H.M., Johnson, D.S. & Dellacoletta, B.A. (1980) Diaryl Ether Formation via Nitro Displacement with 4-Methylphenol and Potassium Carbonate on 4-Nitro-N-methylphthalimide, Journal of Organic Chemistry, (45), pp. 1374-1379. Relles, H.M., Johnson, D.S. & Dellacoletta, B.A. (1980) Diaryl Ether Formation via Nitro Displacement with 4-Methylphenol and Potassium Carbonate on 4-Nitro-N-methylphthalimide, Journal of Organic Chemistry, (45), pp. 1374-1379. Dorogov, M.V., Ivanovsky, S.A., Krasovskaya, G.G. & Abramov, I.G. (1999) The use of potassium bicarbonate as a source of an active deprotonating agent in the reaction of aromatic substitution of the nitro group by nucleophiles, Izvestiya vuzov. Khimiya i khimicheskaya tekhnologiya, 42(6), pp. 69-71 (in Russian). Dorogov, M.V., Ivanovsky, S.A., Krasovskaya, G.G. & Abramov, I.G. (1999) The use of potassium bicarbonate as a source of an active deprotonating agent in the reaction of aromatic substitution of the nitro group by nucleophiles, Izvestiya vuzov. Khimiya i khimicheskaya tekhnologiya, 42(6), pp. 69-71 (in Russian). Plakhtinsky, V.V., Kaninsky, P.S., Mironov, G.S., Yasinsky, O.A. & Abramov, I.G. (1992) Substitution of the nitro group in 4-nitrophthalonitrile using the phenol-metal carbonate system as a nucleophile, Zhurnal organicheskoj khimii, 28(6), pp. 1232-1235 (in Russian). Plakhtinsky, V.V., Kaninsky, P.S., Mironov, G.S., Yasinsky, O.A. & Abramov, I.G. (1992) Substitution of the nitro group in 4-nitrophthalonitrile using the phenol-metal carbonate system as a nucleophile, Zhurnal organicheskoj khimii, 28(6), pp. 1232-1235 (in Russian). Plakhtinsky, V.V., Ustinov, V.A. & Mironov, G.S. (1985) Aromatic nucleophilic substitution involving the nitrite ion, Izvestiya vuzov. Khimiya i khimicheskaya tekhnologiya, 28 (1), pp. 3-18 (in Russian). Plakhtinsky, V.V., Ustinov, V.A. & Mironov, G.S. (1985) Aromatic nucleophilic substitution involving the nitrite ion, Izvestiya vuzov. Khimiya i khimicheskaya tekhnologiya, 28 (1), pp. 3-18 (in Russian).