5062-30-6

Upstream product

• 1074-12-0 phenylglyoxal hydrate 
• 108-24-7 acetic anhydride 
• 127-09-3 sodium acetate 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 621-82-9 Cinnamic acid 
• 13665-04-8 2,2-dibromoacetophenone 
• 64-19-7 acetic acid 
• 98-86-2 acetophenone 

Downstream Products

• 1074-12-0 phenylglyoxal hydrate 
• 100-41-4 ethylbenzene 
• 93-92-5 1-phenylethyl acetate 
• 98-86-2 acetophenone 

Relevant academic research and scientific papers

Solvent-free Chemoselective Synthesis of 1,1-diacetates Catalyzed by Iron Zirconium Phosphate

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.

Hypervalent Iodine Mediated C-C Double Bond Activation: A Cascade Access to α-Keto Diacetates from Readily Available Cinnamic Acids

The reaction of cinnamic acids with (diacetoxyiodo)benzene in 1,2-dichloroethane in the presence of sulfuric acid provides an easy and direct access to the α-keto diacetate framework. This hypervalent iodine mediated oxidative reaction involves a tandem sequence of aryl migration, insertion of an oxygen atom, decarboxylation and diacetoxylation. A reaction mechanism is proposed and discussed in light of control experiments.

Silver acetate mediated acetoxylations of alkyl halides

Silver acetate promotes the acetoxylation of alkyl halides under neutral reaction conditions. The reaction is applicable to primary and activated secondary alkyl halides, and 2,2-dibromoacetophenones for preparing the corresponding acetates in good yields. The presence of ester, amide, nitrile, hydroxy, and OTBDMS functions on the substrate is tolerated.

Preparation of silica-bonded propyl-diethylene-triamine-N-sulfamic acid as a recyclable catalyst for chemoselective synthesis of 1,1-diacetates

A simple and efficient procedure for the preparation of silica-bonded propyl-diethylene-triamine-N-sulfamic acid (SPDTSA) by reaction of 3-diethylenetriamine-propylsilica (DTPS) and chlorosulfonic acid in chloroform is described. Silica-bonded propyl-diethylene-triamine-N-sulfamic acid is employed as a recyclable catalyst for the synthesis of 1,1-diacetates from aromatic aldehydes and acetic anhydride under mild and solvent-free conditions at room temperature. Catalyst could be recycled for several times without any additional treatment.

Reinvestigation of the mechanism of gem-diacylation: Chemoselective conversion of aldehydes to various gem-diacylates and their cleavage under acidic and basic conditions

The mechanism of gem-diacylate formation has been studied extensively using tetrabutylammonium tribromide (TBATB) as the catalyst. The reaction proceeds by a nucleophilic attack of an anhydride on an aldehydic carbonyl group, nucleophilic attack of the hemiacylate intermediate on a second molecule of the anhydride, followed by an intermolecular attack of a second acetate group to regenerate the anhydride. gem-Diacylates of various aliphatic and aromatic aldehydes were obtained directly from the reaction of a variety of aliphatic and aromatic acid anhydrides in the presence of a catalytic quantity of tetrabutylammonium tribromide (TBATB) under solvent-free conditions. A significant electronic effect was observed during its formation as well as deprotection to the corresponding aldehyde. Chemoselective gem-diacylation of the aromatic aldehyde containing an electron-donating group has been achieved in the presence of an aldehyde containing an electron-withdrawing group. Deprotection of the gem-diacylate to the parent carbonyl compound can be accomplished in methanol in presence of the same catalyst. Here again, chemoselective deprotection of the gem-diacylate of a substrate containing an electron-donating group has been achieved in the presence of a substrate containing an electron-withdrawing group. Both the acid and base stability order of the various gem-diacylates examined follow a similar order. The stability order determined from the present study is: gem-dibenzoate > gem-dipivalate > gem-diisobutyrate > gem-diacetate > gem-dipropionate. All the gem-diacylals are more stable under basic conditions than acidic condition. No correlation was found between the stability order and the pKa's of the corresponding acids; rather, the stability order is directly related to the steric crowding around the carbonyl carbon. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Facile synthesis of 1,1-diacetates from aldehydes using environmentally benign solid acid catalyst under solvent-free conditions

Variety of aromatic and aliphatic aldehydes are converted into their 1,1-diacetates in the presence of environmentally benign Mo/TiO 2-ZrO2 solid acid catalyst in good to excellent yields under solvent-free conditions.

LiBF4-mediated conversion of aldehydes to gem-diacetates

An efficient and highly selective method for the conversion of aldehydes to gem-diacetates is described using lithium tetrafluoroborate under mild reaction conditions. Due to the neutral reaction conditions, this method is compatible with acid-sensitive p

Indium trichloride catalyzed chemoselective conversion of aldehydes to gem-diacetates

Aldehydes are chemoselectively converted into the corresponding gem-diacetates at ambient temperature in high to quantitative yields using a catalytic amount of indium (III) chloride. The deprotection of the resulting gem-diacetates is achieved using the same catalyst in the presence of water.

Indium trichloride catalyzed chemoselective conversion of aldehydes to gem-diacetates

Aldehydes are chemoselectively converted into the corresponding gem-diacetates at ambient temperature in high to quantitative yields using a catalytic amount of indium(III) chloride. The deprotection of the resulting gem-diacetates is achieved using the s

Zinc-Promoted Reactions. 9. The Fate of the Cyano Group in the Reduction of Simple Cyanoketones and N-Cyanoamines

The Zn/AcOH reduction of 1 leads only to the carbonyl reduction, while C-decyanation occurs in the case of 2.The mechanism of the latter reaction is discussed.The N-decyanation of N-cyanoamines 3 and 4 involves an ionic mechanism, leading to N-acyl derivatives and isocyanic acid, the latter compound being ultimately reduced to formic acid.