643-79-8Relevant articles and documents
Smart solution chemistry: Prolonging the lifetime of ortho-phthalaldehyde disinfection solutions
Brewer, Bobby N.,Mead, Keith T.,Pittman Jr., Charles U.,Lu, Kaitao,Zhu, Peter C.
, p. 361 - 363 (2006)
The oxidation of ortho-phthalaldehyde to phthalic acid in aqueous solutions can be remedied by the addition of various cyclic acetals, which, when reacted with phthalic acid, yields ortho-phthalaldehyde, thus prolonging the lifetime of the ortho-phthalaldehyde disinfection solution.
Suspending ionic single-atom catalysts in porphyrinic frameworks for highly efficient aerobic oxidation at room temperature
He, Wei-Long,Yang, Xiu-Li,Zhao, Min,Wu, Chuan-De
, p. 43 - 49 (2018)
Room temperature and atmosphere pressure are highly desired catalytic conditions for aerobic oxidation of inert sp3 C–H bonds. To meet this challenge, we developed a simple strategy by suspending ionic single atoms (ISAs) inside the anionic pores of metal–organic frameworks (MOFs). CZJ-22-Cu, consisting of suspended ISA copper(II) inside the anionic pores, exhibits exceptionally high catalytic efficiency in aerobic oxidation of ethers to esters at room temperature and atmosphere pressure, in which turnover number (TON) 77,100 and turnover frequency (TOF) 7710 h?1 have been realized for aerobic oxidation of isobenzofuran. The unmatched catalytic properties of CZJ-22-Cu are attributed to the unique features of suspended ISAs inside the anionic pores, which result in high surface free energy of redox-active centers, and the substrate-selective accumulation nature of the inside pores, which would significantly improve the reactivity and reaction rate.
Synthesis of new Zn (II) complexes for photo decomposition of organic dye pollutants, industrial wastewater and photo-oxidation of methyl arenes under visible-light
Ahemed, Jakeer,Bhongiri, Yadagiri,Chetti, Prabhakar,Gade, Ramesh,Kore, Ranjith,Pasha, Jakeer,Pola, Someshwar,Rao D, Venkateshwar
, (2021/07/28)
Synthesis of new Schiff's base Zn-complexes for photo-oxidation of methyl arenes and xylenes are reported under visible light irradiation conditions. All the synthesized new ligands and Zn-complexes are thoroughly characterized with various spectral analyses and confirmed as 1:1 ratio of Zn and ligand with distorted octahedral structure. The bandgap energies of the ligands are higher than its Zn-complexes. These synthesized new Zn(II) complexes are used for the photo-fragmentation of organic dye pollutants, photodegradation of food industrial wastewater and oxidation of methyl arenes which are converted into its respective aldehydes with moderate yields under visible light irradiation. The photooxidation reaction dependency on the intensity of the visible light was also studied. With the increase in the dosage of photocatalyst, the methyl groups are oxidized to get aldehydes and mono acid products, which are also identified from LC-MS data. Finally, [Zn(PPMHT)Cl] is with better efficiency than [Zn(PTHMT)Cl] and [Zn(MIMHPT)Cl] for oxidation of methyl arenes is reported under visible-light-driven conditions.
Oxidaition of cyclic benzylic ethers by an electronically tuned nitroxyl radical
Furuta, Takumi,Hamada, Shohei,Kawabata, Takeo,Kobayashi, Yusuke,Yano, Kyoko
supporting information, (2021/10/04)
The reactivity of an electronically tuned nitroxyl radical catalyst for the oxidation of cyclic benzylic ethers has been investigated. The oxidation of phthalan resulted in oxidative cleavage of the saturated ring to give an aromatic dialdehyde. Additionally, oxidation of isochromans afforded isochromanones, which are often seen in natural products, in a rapid manner.
A Magnetically Recyclable Palladium-Catalyzed Formylation of Aryl Iodides with Formic Acid as CO Source: A Practical Access to Aromatic Aldehydes
You, Shengyong,Zhang, Rongli,Cai, Mingzhong
supporting information, p. 1962 - 1970 (2021/01/25)
A magnetically recyclable palladium-catalyzed formylation of aryl iodides under CO gas-free conditions has been developed by using a bidentate phosphine ligand-modified magnetic nanoparticles-anchored- palladium(II) complex [2P-Fe 3O 4@SiO 2-Pd(OAc) 2] as catalyst, yielding a wide variety of aromatic aldehydes in moderate to excellent yields. Here, formic acid was employed as both the CO source and the hydrogen donor with iodine and PPh 3as the activators. This immobilized palladium catalyst can be obtained via a simple preparative procedure and can be facilely recovered simply by using an external magnetic field, and reused at least 9 times without any apparent loss of catalytic activity.
New methods to synthesize phthalaldehyde and its diacetals
Gazizov,Khairullin,Ivanova, S. Yu.,Kirillina, Yu. S.,Romanenko,Gazizova
, p. 1878 - 1882 (2019/10/21)
A new synthesis of phthalaldehyde that avoided formation of HBr involved treatment of 1,2-bis(dibromomethyl)benzene with trimethyl orthoformate (1: 6, 90 °C, 10 mol.% ZnCl2) to obtain acyclic diacetal without admixture of cyclic one (1,3-dimethoxy-1,3-dihydrobenzo-[c]furan) followed by hydrolysis to give the target dialdehyde. Phthalaldehyde reacted with CH(OMe)3 in the presence of trifluoroacetic acid to yield exclusively cyclic diacetal. Acyclic diacetal was phosphorylated by treatment with secondary chlorophosphines and by the reaction with PCl3 followed by treatment with PIII acid ester.
Synthesis of Phthalic Aldehyde and Its Diacetals
Khairullin,Gazizov,Kirillina, Yu. S.,Ivanova, S. Yu.,Khairullina,Gazizova
, p. 2178 - 2184 (2020/01/08)
Acyclic phthalaldehyde diacetal without cyclic 1,3-dihydro-1,3-dimethoxybenzo[c]furan impurity has been obtained via the reaction of 1,2-bis(dibromomethyl)benzene with trimethyl orthoformate (1:6) at 90°C in the presence of 10 mol% of ZnCl2. Hydrolysis of phthalaldehyde diacetal has led to the formation of phthalaldehyde without HBr evolution. The reaction of phthalaldehyde with trimethyl orthoformate in the presence of trifluoroacetic acid has proceeded abnormally, with the formation of the cyclic diacetal. The acyclic diacetal has been phosphorylated by chlorophosphines and the action of PCl3 and a P(III) acid ester in sequence.
Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: Toward the emergence of new building blocks
Moitessier, Clémence,Rifai, Ahmad,Danjou, Pierre-Edouard,Mallard, Isabelle,Cazier-Dennin, Francine
, p. 721 - 726 (2019/04/17)
4-Methoxy-ortho-phthalaldehyde and 4-hydroxy-ortho-phthalaldehyde are potentially useful molecules for fluorimetric analysis of a variety of amines and for the elaboration of complex molecular architectures. Nevertheless, literature generally describes their synthesis in very low yield (below 5%), mainly due to the inefficiency of the last oxidation step. In this paper, we report a reliable synthesis of 4-substituted-ortho-phthalaldehyde analogues in 51% overall yield owing to the addition of a protecting step of the unstable key intermediate 4,5-dihydroisobenzofuran-5-ol. Oxidation and deprotection steps were also studied in order to provide an effective availability of these two dialdehyde compounds that may increase their future applications.
Synthesis of 1,2-phenylenedimethanols by base-promoted reduction of isobenzofuran-1(3H)-ones with silane
Liu, Bin,Zhou, Xigeng
supporting information, p. 725 - 728 (2018/12/11)
An efficient method for preparation of substituted 1,2-phenylenedimethanols and aliphatic 1,4-diols that are valuable intermediates in organic synthesis, has been developed by the base-promoted reduction of isobenzofuran-1(3H)-ones and γ-lactones with silane under mild conditions. Compared with traditional procedures using stoichiometric amounts of metal hydrides and alkyl reductants, the present method avoids the use of sensitive reagents and is operationally simple and a broad variety of functional groups are tolerated.
Selective vapor-phase oxidation of o-xylene to phthalic anhydride over Co-Mn/H3PW12O40@TiO2 using molecular oxygen as a green oxidant
Masoomi, Kianoosh,Ghiaci, Mehran,Botelho do Rego
, (2018/08/22)
The oxidation of o-xylene to phthalic anhydride over Co-Mn/H3PW12O40@TiO2 was investigated. The experimental results demonstrated that the prepared catalyst effectively catalyzed the oxidation of o-xylene to phthalic anhydride. Also, the synergistic effect between three metals plays vital roles in this reaction. From a green chemistry point of view, this method is environmentally friendly due to carrying out the oxidation in a fixed-bed reactor under solvent-free condition and using molecular oxygen as a green and cheap oxidizing agent. The resulting solid catalysts were characterized by FT-IR, XRD, XPS, ICP-OES, FESEM, TEM, EDX, DR-UV spectroscopy, BET and thermogravimetric analysis. The oxidation of o-xylene yields four products: o-tolualdehyde, phthaldialdehyde, phthalide and finally phthalic anhydride as the main product. The reaction conditions for oxidation of o-xylene were optimized by varying the temperature, weight hourly space velocity and oxygen flow rate (contact time). The optimum weight percentage of phosphotungstic acid (HPW) and Co/Mn for phthalic anhydride production were 15?wt % and 2?wt%, respectively. The best Co/Mn ratio was found to be 10/1. Oxygen flow rate was very important on the phthalic anhydride formation. The optimum conditions for oxidation of o-xylene were T?=?370?°C, WHSV?=?0.5?h?1 and oxygen flow rate?=?10?mL?min?1. Under optimized conditions, a maximum of 88.2% conversion and 75.5% selectivity to phthalic anhydride was achieved with the fresh catalyst. Moreover, reusability of the catalyst was studied and catalytic activity remained unchanged after at least five cycles.
