24653-82-5Relevant academic research and scientific papers
(NH4)3PW12O40 as an efficient and reusable catalyst for the synthesis and deprotection of 1,1-diacetates
Satam, Jitendra R.,Jayaram, Radha V.
, p. 595 - 602 (2008)
An efficient method for the synthesis of 1,1-diacetates (acylals) from different aldehydes in the presence of (NH4)3PW12O40 and acetic anhydride under solvent-free conditions at ambient temperature is achieved. Selective conversion of aldehydes was observed in the presence of ketones. The deprotection of acylals has also been achieved using (NH4)3PW12O40 in methanol. The catalyst was found to possess good activity and considerable level of reusability. Copyright Taylor & Francis Group, LLC.
N-Propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) as a green and reusable heterogeneous nanocatalyst for the chemoselective preparation and deprotection of acylals
Sajjadifar, Sami,Nasri, Parastoo
, p. 6677 - 6689 (2017/10/06)
Abstract: N-propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) was simply synthesized and used as a highly efficient, environmentally friendly, and chemoselective catalyst for the synthesis of 1,1-diacetates (acylals) from the one-pot condensation reaction of various aromatic aldehydes with acetic anhydride, in high yield of products (86–96%) and short reaction time (20–60?min) under solvent-free conditions at room temperature. In addition to these results, we further studied the possibility of deprotection of the resulting acylals into benzaldehyde derivatives in this catalytic system by the addition of water. More importantly, noteworthy advantages of this study are non-use of toxic organic solvents and catalysts, simple work-up procedure, short reaction time, high yield of products, and recovery and reusability of MNPs-PSA by an external magnet. Graphical Abstract: A simple and highly efficient procedure for the protection of various aldehydes with acetic anhydride in the presence of N-propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) is reported. We further studied the possibility of deprotection of the resulting acylals into benzaldehyde derivatives in this catalytic system by the addition of water as a green solvent. The catalyst was reused several times without loss of its catalytic activity.
Solvent-free Chemoselective Synthesis of 1,1-diacetates Catalyzed by Iron Zirconium Phosphate
Karimi, Hirbod
, p. 1000 - 1010 (2015/12/01)
In the present study, a mild, rapid, and efficient method for the protection of aldehydes with acetic anhydride (AA) in the presence of iron zirconium phosphate (ZPFe), at room temperature is reported. Selective conversion of aldehydes was observed in the presence of ketones. Under these conditions, different aldehydes bearing electron-withdrawing and electron-donating substituents were reacted with AA and the corresponding 1,1-diacetates (acylals) were obtained in high to excellent yields. The steric and electronic properties of the different substrates had a significant influence on the reaction conditions. Also, the deprotection of 1,1-diacetates has been achieved using this catalyst in water. The catalyst was characterized by several physico-chemical techniques. It was recovered easily from the reaction mixture, regenerated, and reused at least 7 times without significant loss in catalytic activity. This protocol has the advantages of easy availability, stability, reusability of the eco-friendly catalyst, chemoselectivity, simple experimental and work-up procedure, solvent-free conditions and only a stoichiometric amount of AA is needed.
Zinc zirconium phosphate as an efficient catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions
Hajipour, Abdol R,Karimi, Hirbod
, p. 1945 - 1955 (2015/12/30)
In the present study, a mild, rapid, and efficient method for the protection of aldehydes with acetic anhydride (AA) in the presence of zinc zirconium phosphate (ZPZn) as a nano catalyst, at room temperature is reported. Selective conversion of aldehydes was observed in the presence of ketones. Under these conditions, different aldehydes bearing electron-withdrawing and electron-donating substituents were reacted with AA and the corresponding 1,1-diacetates (acylals) were obtained in high to excellent yields. The steric and electronic properties of the different substrates had a significant influence on the reaction conditions. Also, the deprotection of 1,1-diacetates has been achieved using this catalyst in water. This nanocatalyst was characterized by several physico-chemical techniques. It was recovered easily from the reaction mixture, regenerated and reused at least 7 times without significant loss in catalytic activity. This protocol has the advantages of easy availability, stability, reusability of the eco-friendliness, chemoselectivity, simple experimental and work-up procedure, solvent-free conditions and usage of only a stoichiometric amount of AA.
A highly efficient solvent-free acetalization of aldehydes to 1,1-diacetates catalyzed by SiO2-Pr-SO3H
Ziarani, Ghodsi Mohammadi,Badiei, Alireza,Shahjafari, Fatemeh,Pourjafar, Taiiebeh
experimental part, p. 10 - 13 (2012/05/19)
1,1-Diacetates are prepared in excellent yields from aldehydes and acetic anhydride under solvent-free conditions at room temperature in short reaction times using catalytic amount of sulfonic acid functionalized silica (SiO 2-Pr-SO3H) which could be easily handled and removed from the mixture of reaction.
A new and efficient procedure for the production of 1,1-diacetate from corresponding aldehydes promoted by silica chromate (SiO2-O-CrO 2-O-SiO2)
Bamoniri, Abdolhamid,Ghorbani-Choghamarani, Arash,Mirjalili, Bi Bi Fatemeh
experimental part, p. 381 - 388 (2011/04/22)
Chemical Equation Presented A wide range of aromatic aldehydes has been selectively converted to 1,1-diacetates using silica chromate (SiO 2-O-CrO2-O-SiO2) under solvent-free conditions at room temperature in moderate to good yields. This protocol is mild and efficient compared to other reported methods. Copyright Taylor & Francis Group, LLC.
An efficient and chemoselective procedure for acylal synthesis
Fan, Da-He,Wang, Hui,Mao, Xing-Xing,Shen, Yong-Miao
experimental part, p. 6493 - 6501 (2010/11/04)
A novel heterogeneous efficient procedure has been developed for the chemoselective synthesis of acylals (1,1-diacetates) under solvent-free conditions. A novel catalyst prepared by the sulfuric acid catalyzed copolymerization of p-toluenesulfonic acid and paraformaldehyde displays extremely high activities for the title reactions, affording average yields over 90% within several minutes. A comparative study showed that the novel catalyst has much higher activity than other catalysts used for this purpose. Besides, the novel catalyst displays chemoselectivity for the protection of aldehydes in the presence of ketones. In addition the high acidity (4.0 mmol/g), thermal stability (200 °C) and easy reusability make the novel catalyst one of the best choices for the process.
Silica phosphoric acid: An efficient and recyclable catalyst for the solvent-free synthesis of acylals and their deprotection in MeOH
Zhang, Fuyi,Liu, Hong,Zhang, Qing-Ju,Zhao, Yu-Fen,Yang, Feng-Ling
experimental part, p. 3240 - 3250 (2010/12/24)
Silica phosphoric acid was used as an efficient, mild, and recyclable solid catalyst for the synthesis of acylals from various structurally diverse aldehydes and acetic anhydride under solvent-free conditions. The acylation of aldehydes was highly chemoselective, and no ketone was acylated, which provided a method for the synthesis of acylals from aldehydes in the presence of ketones. Silica phosphoric acid-catalyzed deprotection of acylals to the corresponding aldehydes in MeOH has also been developed with excellent yield. The deprotection of the acylals of aromatic aldehydes took priority over those of aliphatic aldehydes. Copyright Taylor & Francis Group, LLC.
Chemoselective synthesis of 1,1-diacetates from aldehydes using anhydrous cobalt(II) bromide under solvent-free conditions
Meshram, Gangadhar A.,Patil, Vishvanath D.
experimental part, p. 442 - 449 (2010/04/02)
A mild and efficient method has been developed for the chemoselective preparation of 1,1-diacetates (acylals) from aldehydes catalyzed in the presence of a catalytic amount (0.1mmol) of anhydrous cobalt(II) bromide under solvent-free conditions. The remarkable selectivity under mild and neutral conditions, excellent yields, short reaction time, and easily available and inexpensive catalyst are important features of this method.
Solvent free diacetylation of aldehydes using a solid acid under microwave irradiation and a simple route to their regeneration
Barua, Akashi,Das, Pranab J.
, p. 938 - 941 (2008/12/23)
A simple solvent-free microwave mediated procedure for the selective protection of aldehydes by conversion to their 1,1-diacetates is reported. The resultant diacetates were deprotected to generate the aldehyde using aqueous formic acid in the presence of a surfactant in high yield.
