29949-19-7

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 1765, 1983 DOI: 10.1021/jo00158a036Tetrahedron Letters, 36, p. 601, 1995 DOI: 10.1016/0040-4039(94)02292-J

InChI:InChI=1/C11H11NO6/c1-7(13)17-11(18-8(2)14)9-4-3-5-10(6-9)12(15)16/h3-6,11H,1-2H3

Upstream product

• 108-24-7 acetic anhydride 
• 99-61-6 3-nitro-benzaldehyde 
• 581-55-5 benzylidene 1,1-diacetate 
• 7697-37-2 nitric acid 
• 100-52-7 benzaldehyde 
• 104-87-0 4-methyl-benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 86119-84-8 phosphoric acid 

Downstream Products

• 614-48-2 (E)-3-nitrochalcone 
• 99-61-6 3-nitro-benzaldehyde 
• 108-44-1 1-amino-3-methylbenzene 
• 23229-30-3 3-nitrophenyl-1,3-dithiolane 
• 71787-52-5 1-(3-nitrophenyl)-3-buten-1-ol 
• 108714-19-8 (E)-1-(3′-aminophenyl)-3-phenylprop-2-en-1-one 
• 107523-37-5 [1-(3-nitro-phenyl)-3-oxo-3-phenyl-propylsulfanyl]-acetic acid 
• 110531-69-6 3-(3-nitro-phenyl)-1,3-diphenyl-propan-1-one 
• 111294-68-9 3-(4-methoxyphenyl)-3-(3-nitrophenyl)-1-phenylpropan-1-one 
• 113651-72-2 [1-(3-nitro-phenyl)-3-oxo-3-phenyl-propyl]-malonic acid diethyl ester 
• 113651-73-3 [3-(3-nitro-phenyl)-3-oxo-1-phenyl-propyl]-malonic acid diethyl ester 
• 42792-81-4 α,α'-bis(3-nitrobenzylidene)cyclohexanone 
• 123371-44-8 nifetepimine 
• 1026157-82-3 1-(3-nitrophenyl)pentyl acetate 

Relevant academic research and scientific papers

Solvent-free chemoselective synthesis of 1,1-diacetates catalyzed by Cu(NO3)2·3H2O

1,1-Diacetates have been synthesized by the reaction of a variety of aldehydes with acetic anhydride in the presence of cupric nitrate as catalyst under solvent-free conditions. Ketones were not converted to the corresponding diacetates under these conditions. Copyright Taylor & Francis Group, LLC.

A stable intermediate: a new insight into the mechanism of Lewis acids-promoted formation of acylals from aldehydes

Treatment of m-nitrobenzaldehyde with acetic anhydride in the presence of Lewis acids, such as InBr3, ZnBr2, Cu(OTf)2, gives a stable intermediate at the initial stage of reaction. Based on this new organic compound characterized by X-ray single crystal diffraction, a new mechanism for Lewis acids-promoted formation of acylals from aldehydes is proposed. Exchange reaction with different ratio of acetic anhydride to propionic anhydride, in the presence of Lewis acids, is studied.

Solid superacids as catalysts for the synthesis of acylals from aldehydes and acetic anhydride

Sulfated tin, aluminum, and titanium oxides are efficient catalysts for reactions of aldehydes with acetic anhydride leading to acylals.

Application of poly(Vinylbenzyltrimethylammonium tribromide) resin as an efficient polymeric catalyst in the acetalization and diacetylation of benzaldehydes

The applications of a new supported tribromide reagent (poly(vinylbenzyltrimethylammonium tribromide) resin) were reported. This supported tribromide resin was used as a catalyst in the acetalization and diacetylation of benzaldehydes under mild conditions with high efficiency. The effects of solvents, and amount of the supported tribromide resin on the reactions were investigated. Under the optimal conditions, most of acetal and 1,1-diacetates of benzaldehydes were selectively obtained in excellent yields.

Chemoselective synthesis of 1,1-diacetates under solvent-free condition using efficient heterogeneous ecofriendly catalyst: P2O5/kaolin

An efficient and chemoselective method for the preparation of acylals from different aldehydes and acetic anhydride using.....kaolin supported catalyst (P2O5). under solvent-free conditions is described herein. The present protocol offers several advantages including use of inexpensive and non-toxic catalyst support i.e., natural kaolin. Preparation of the supported catalyst is easy, the process is simple in operation, maintaining solvent free conditions, with short reaction times, high yields and affording selective protection of aldehyde in presence of ketone.

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

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.

Microwave-assisted green synthesis of 1,1-diacetates (acylals) using selectfluor as an environmental-friendly catalyst under solvent-free conditions

An efficient and simple procedure has been developed for the acetylation of aldehyde by selectfluor [1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane bis(tetrafluoroborate)] as a chemoselective and environmentally friendly catalyst under solvent-free conditions or microwave irradiation. The application of microwave irradiation improved the yields and reduced the reaction times. In this study, selective conversion of aldehydes was observed in the presence of ketones, and the deprotection of 1,1-diacetates has also been achieved using selectfluor in water as green solvent in reflux conditions. The methodology provides synergy of microwave irradiation which offers several advantages such the simple work-up procedure, short reaction time, excellent yields and environmentally benign procedure.

Synthesis of 1,1-diacetates catalyzed by cellulose sulfonic acid from aldehydes and acetic anhydride

1,1-Diacetates have been synthesized in good to excellent yields via a reaction of corresponding aldehydes and acetic anhydride in the presence of cellulose sulfonic acid as a heterogeneous catalyst at room temperature. The protection of aldehydes generated an anhydrodimer as single product under similar reaction conditions. The catalysis is equally applicable for the deprotection of acylal in acetonitrile.

Preparation of 1,1-diacetates from aldehydes by LiBH4 and Ac2O in the presence of cation exchange resin

A variety of 1,1-diacetates have been produced from the corresponding aldehydes (1 mmol) by LiBH4(1.25 mmol) and Ac2O (1 mL) in the presence of DOWEX(R)50WX4 (0.5 g) as a cation exchange resinwithin 10 min at room temperature with excellent yields of the products (93-97%).

NaBH4/Ac2O/DOWEX(R)50WX4: A convenient system for fast preparation of gem-diacetates from aldehydes

Reductive-acylalation of aldehydes has been carried out by NaBH 4/Ac2O/DOWEX(R)50WX4 system. A variety of aldehydes (1 mmol) have been reacted with Ac2O (0.5 mL) and NaBH4 (1 mmol) in the presence of DOWEX(R)50WX4 (0.5 g) for the preparation of their corresponding acylals within 1 min at room temperature with excellent yields of the products (90-95%). Ketones do not react with this system.