Synthesis of fatty 1,2,4-trioxanes by peracetalisation of β-hydroxy hydroperoxides

Synthesis ◽  
2021 ◽  
Author(s):  
Thomas De Dios Miguel ◽  
Dan Louvel ◽  
Killian Onida ◽  
Adeline Lavoignat ◽  
Stephane Picot ◽  
...  
Keyword(s):  
Sulfonic Acid ◽  
Heterogeneous Catalysts ◽  
Antimalarial Activity ◽  
Acid Catalyst ◽  
Methyl Tert Butyl Ether ◽  
Significant Activity ◽  
Butyl Ether ◽  
Aliphatic Aldehydes ◽  
Toluene Sulfonic Acid ◽  
Optimized Conditions

The peracetalisation of a β-hydroxy hydroperoxide derived from methyl oleate was studied using benzaldehyde as a model substrate to give the corresponding fatty 1,2,4-trioxane. The desired product was obtained as a mixture of regioisomers but only one diastereoisomer of each was formed. The nature of the acid catalyst was studied and both para-toluene sulfonic acid (PTSA) and Amberlyst A35 (A35) were found to be efficient homogeneous and heterogeneous catalysts, respectively. The nature of the solvent was also investigated and ethereal solvents such as 2-methyltetrahydrofuran (2-MeTHF), methyl tert-butyl ether (MTBE) and cyclopentyl methyl ether (CPME) gave the best NMR yield (85%) for the preparation of the fatty trioxane. The optimized conditions were applied to a range of aromatic and aliphatic aldehydes and the corresponding 1,2,4-trioxanes were isolated with 30-91% yields (21 examples). The antimalarial activity of 3 trioxanes was studied against Plasmodium falciparum, however, no significant activity was detected (IC50 > 1600 nM).

Polymer impregnated sulfonated carbon composite solid acid catalyst for alkylation of phenol with methyl-tert-butyl ether

RSC Advances ◽  
2015 ◽  
Vol 5 (5) ◽  
pp. 3286-3290 ◽  
Author(s):  
Praveen K. Khatri ◽  
Manvi Manchanda ◽  
Indrajit K. Ghosh ◽  
Suman L. Jain
Keyword(s):  
Composite Material ◽  
Alkylating Agent ◽  
Solid Acid ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Carbon Composite ◽  
Methyl Tert Butyl Ether ◽  
Butyl Ether ◽  
Autogenous Pressure ◽  
Composite Solid

A polymer impregnated sulfonated carbon composite solid acid catalyst was synthesized via sulfonation of a composite material and used for the alkylation of phenol using methyl-tert-butyl ether as an alkylating agent in a pressure reactor under autogenous pressure.

scholarly journals An efficient and highly selective ortho-tert-butylation of p-cresol with methyl tert-butyl ether catalyzed by sulfonated ionic liquids

2014 ◽  
Vol 79 (11) ◽  
pp. 1337-1346 ◽  
Author(s):  
Reza Alamdari ◽  
Faezeh Zamani ◽  
Negar Zekri
Keyword(s):  
Ionic Liquids ◽  
Sulfonic Acid ◽  
Methyl Tert Butyl Ether ◽  
Butyl Ether ◽  
Tert Butyl ◽  
Green Conditions

A novel series of sulfonic acid-functionalized ionic liquids (SFILs) was found to act as efficient catalysts for ortho-tert-butylation of p-cresol with methyl tert-butyl ether (MTBE) as the tert-butylating agent without an added solvent. The mono o-tert-butylated product was obtained in up to 80.4% isolated yield and 95.2% selectivity under such green conditions. No O-tert-butylated byproducts were formed.

Acid-Catalyzed Condensation of o-Phenylenediammines and o-Aminophenols with α-Oxodithioesters: A Divergent and Regio­selective Synthesis of 2-Methylthio-3-aryl/Heteroarylquinoxalines and 2-Acylbenzoxazoles

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4205-4214 ◽  
Author(s):  
Kuppalli R Kiran ◽  
Toreshettahally R Swaroop ◽  
Kodipura P Sukrutha ◽  
Jeegundipattana B Shruthi ◽  
Seegehally M Anil ◽  
...  
Keyword(s):  
Tyrosine Phosphorylation ◽  
Binding Affinity ◽  
Carbonyl Group ◽  
Sulfonic Acid ◽  
Acid Catalyst ◽  
Biological Targets ◽  
Dual Specificity ◽  
Toluene Sulfonic Acid ◽  
Acid Catalyzed

o-Phenylenediammines and o-aminophenols were reacted with α-oxodithioesters in a highly regioselective fashion to give 2-methylthio-3-aryl/heteroarylquinoxalines and 2-acylbenzoxazoles in 55–94% and 45–86%, respectively, in the presence of p-toluene sulfonic acid catalyst. Control experiments involving reaction of aniline with a α-oxodithioester indicated that the thiocarbonyl group is more reactive than the carbonyl group. Based on this, probable mechanisms for the formation of quinoxalines and benzoxazoles are given. Biological targets of the quinoxalines and benzoxazoles were identified by bioinformatics. It was found that quinoxalines have good binding affinity with human dual-specificity tyrosine-phosphorylation-regulated kinase 1A and benzoxazoles with human carboxylesterase.

scholarly journals Grinding Technique on Synthesis of Calixarene and Its Derivatives

2020 ◽  
Vol 20 (2) ◽  
pp. 117-123
Author(s):  
Susy Yunita Prabawati ◽  
Afifah Mufidati ◽  
Titis Ratna Djuwita ◽  
Titis Ratna Djuwita ◽  
Siti Nur Ngaini
Keyword(s):  
Sulfonic Acid ◽  
Electrophilic Substitution ◽  
Acid Catalyst ◽  
Ftir Analysis ◽  
Substitution Reactions ◽  
Alkaline Catalyst ◽  
Methylene Bridge ◽  
Product Characterization ◽  
Toluene Sulfonic Acid ◽  
Grinding Technique

The synthesis of p-t-butylcalix[6]arene (PK[6]A) and calixresorcinarene derivative compounds, namely C-para-dimethylamino-phenylcalix[4]resorcinarene (CPDAK[4]R) and C-4-hydroxy-phenylcalix[4]-resorcinarene (CHK[4]R), had been carried out by grinding technique. The grinding technique was done with the absence of solvents so that it minimized the waste. Synthesis occurred through electrophilic substitution reactions with KOH as an alkaline catalyst and p-toluene sulfonic acid as an acid catalyst. The three calixarene products were in the form of crystalline solids with a melting point of more than 300°C, insoluble in water with yields of 62.58; 61.94 and 97.49%, respectively. Product characterization using FTIR analysis showed the vibration of the methylene bridge (-CH2-) at a wavenumber of 1473.62 cm-1 and LC-MS analysis for (PK[6]R) showed that the molecular weight was 974.77 g/mole. While the analysis of (CPDAK[4]R) and (CHK[4]R) with 1H NMR showed the presence of protons from the methine bridge (-CH-) that appear at the chemical shift of  4.950 and 3.078 ppm.

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