1575-87-7Relevant academic research and scientific papers
Study of reaction of isomeric acetoxytoluenes with ozone in liquid phase in the presence of manganese bromide catalyst
Galstyan,Sedykh
, p. 948 - 952 (2010)
The kinetics of the ozone reaction with isomeric acetoxytoluenes in acetic anhydride in the presence of sulfuric acid and mixed manganese bromide catalyst was studied. Under these conditions it is possible to stop the oxidation process at the stage of formation of hydroxybenzaldehydes in the form of the respective acetoxybenzylidendiacetates (63-70%). The reaction products contain also acetoxybenzyl acetate (16-18%) and a small amount of acetoxybenzyl bromide (2%). The mechanism of oxidation-reduction catalysis with manganese bromide complex explaining the experimental data was considered. Pleiades Publishing, Ltd., 2010.
Oxidation of 2-acetoxytoluene with ozone in acetic anhydride
Galstyan
, p. 1690 - 1694 (2008)
Kinetics and mechanism of the reaction of ozone with 2-acetoxytoluene in acetic anhydride in the presence of sulfuric acid were studied. It was shown that the prevailing reaction route under these conditions is ozonolysis (89%), and the selectivity of the oxidation of the substrate by the methyl group is no higher 9%. However, in the presence of manganese(II) sulfate as a catalyst, the selectivity increases to 76%. The major reaction products were 2-acetoxybenzyl acetate (59%) and 2-acetoxybenzylidene diacetate (17%). In the presence of a manganese bromide catalyst, the oxidation depth increases, and the major reaction product is already 2-acetoxybenzylidene (66%), while the yield of 2-acetoxybenzyl acetate is 15%. The mechanism of the redox catalysis is considered, that explains the experimental results.
Practical way for the synthesis of 3,3′-bis-substituted benzo[d][1,2]oxaphosphole 2-oxides by phosphonylation of in situ generated o-quinone methides
He, Xinchun,Lv, Wenwen,Shi, Xiaomeng,Wei, Hao,Shi, Min,Wang, Feijun
, p. 1038 - 1041 (2018)
Phosphonylation of the pretreated 2-(hydroxymethyl)phenol derivatives with acetic anhydride using trialkylphosphites as the nucleophilic reagents was reported, providing a practical way to the synthesis of novel highly steric 3,3′-bis-substituted benzo[d][1,2]oxaphosphole 2-oxides.
Reactions of o-cresol with ozone in acetic anhydride
Galstyan,Sedykh,Lysak
, p. 118 - 122 (2008)
The kinetics of o-cresol oxidation with ozone in acetic anhydride was studied. It was shown that o-cresol was acylated in acetic anhydride to give o-cresyl acetate. Ozone attacks the C=C bonds of the aromatic ring of o-cresyl acetate to give unsaturated peroxide compounds. The composition of the oxidation products alters when the ozonation is carried out in the presence of catalytic amounts of sulfuric acid. Along with the products of the destructive oxidation of the aromatic ring, the methyl group oxidation products appeared as the acyl derivatives o-acetoxybenzyl alcohol and o-acetoxybenzaldehyde, a form that is more stable toward the action of ozone (10%). The addition of manganese(II) acetate to the reaction mixture increases the methyl group oxidation selectivity to 75%. The mechanism of the ozone reaction with o-cresol in acetic anhydride that explains the obtained results is discussed.
4-Imidazol-1-yl-butane-1-sulfonic acid ionic liquid: Synthesis, structural analysis, physical properties and catalytic application as dual solvent-catalyst
Khaligh, Nader Ghaffari,Mihankhah, Taraneh,Johan, Mohd Rafie,Juan, Joon Ching
, p. 866 - 878 (2019/07/12)
4-Imidazol-1-yl-butane-1-sulfonic acid (ImBu-SO3H) has been successfully synthetized and fully characterized by FT-IR and high-resolution NMR spectroscopy (1H, 13C). The “plausible” alternative structures of ImBu-SO3H were discussed on the basis of its NMR data. The ionic liquid showed interesting dual solvent-catalyst property, which was studied experimentally for the acetylation of a variety of functionalized alcohols, phenols, thiols, amines and α-tocopherol (α-CTP) as the most active form of vitamin E with acetic anhydride and which provided good yields within a short reaction time. ImBu-SO3H was successfully recycled by product extraction with an average recovered yield of 82% for 5 subsequent runs. The catalytic activity of the recycled ImBu-SO3H showed almost no loss even after five consecutive runs.
Acetylation of alcohols and phenols by zinc zirconium phosphate as an efficient heterogeneous catalyst under solvent-free conditions
Hajipour, Abdol Reza,Karimi, Hirbod,Karimzadeh, Morteza
, p. 1461 - 1472 (2014/09/30)
An efficient method for the acetylation of a wide range of alcohols as well as phenols with acetic anhydride in good to excellent yields under solvent-free conditions, using zinc zirconium phosphate as the catalyst was investigated. The catalyst was characterized by XRD, inductivity coupled plasma-optical emission spectroscopy, and scanning electron microscope. Products are easily isolated and the protocol is mild and green, compared to the existing methods. Graphical abstract: [Figure not available: see fulltext.]
Poly(N-vinylimidazole) as an efficient catalyst for acetylation of alcohols, phenols, thiols and amines under solvent-free conditions
Khaligh, Nader Ghaffari
, p. 99 - 110 (2013/04/10)
Poly(N-vinylimidazole) is able to promote instantaneous quantitative acetylation of a variety of functionalized alcohols, phenols, thiols and amines with acetic anhydride at room temperature under solvent-free conditions. This new method consistently has excellent yields and the catalyst can be reused and recovered several times. Furthermore, the reaction can even be carried out on a larger scale. The Royal Society of Chemistry.
A succinimide-N-sulfonic acid catalyst for acetylation reactions in absence of a solvent
Shirini, Farhad,Khaligh, Nader Ghaffari
, p. 695 - 703 (2013/08/25)
A small amount of succinimide-N-sulfonic acid efficiently catalyzed the acetylation of a variety alcohols, phenols, thiols, amines and aldehydes with acetic anhydride at room temperature under solvent free conditions. This catalyst has the advantages of excellent yields and short reaction times and the reaction can be carried out on a large scale, which makes it potentially useful for industrial applications.
Preparation, characterization and use of poly(4-vinylpyridinium) perchlorate as a new, efficient, and versatile solid phase catalyst for acetylation of alcohols, phenols and amines
Khaligh, Nader Ghaffari
, p. 90 - 100 (2012/11/06)
Poly(4-vinylpyridine) perchlorate, is a supported, recyclable, eco-benign catalyst for the reaction acetylation of structurally diverse alcohols, phenols and amines at room temperature under solvent-free conditions. The catalyst was studied by FT-IR, X-ray diffraction, Scanning Electron Microscope and Thermo-gravimetric Analyses. All the products were extensively characterized by 1H NMR, FT-IR, GC-MS and melting point analyses. The catalyst can be recovered and reused without loss of activity. The work-up of the reaction consists of a simple filtration, followed by concentration of the crude product and purification. It is important to point out that a large-scale reaction is possible using a same amount of catalyst.
P2O5/Al2O3 AS an efficient heterogeneous catalyst for the acetylation of alcohols, phenols, thiols, and amines under solvent-free conditions
Zarei, Amin,Hajipour, Abdol R.,Khazdooz, Leila
experimental part, p. 1772 - 1785 (2011/06/20)
A convenient, rapid, and efficient method for the acetylation of alcohols, phenols, thiols, and amines has been developed by using acetic anhydride in the presence of a catalytic amount of P2O5/Al 2O3 under solvent-free conditions at room temperature. This reaction was studied under different conditions, and several solvents were examined for this conversion. However, in terms of reaction time and yield, it was found that the best result was obtained when the reaction was carried out under solvent-free conditions. Racemization of optically active alcohols and epimerization of sugars were not observed. The use of nontoxic and inexpensive materials, simple and clean workup, short reaction times, and good yields of the products are the advantages of this method.
