59184-17-7

Upstream product

• 108-24-7 acetic anhydride 
• 591-31-1 3-methoxy-benzaldehyde 

Downstream Products

• 114095-72-6 1-(3-methoxyphenyl)-3-butenyl acetate 
• 591-31-1 3-methoxy-benzaldehyde 

Relevant academic research and scientific papers

SiO2@FeSO4 nano composite as nanocatalyst for the green synthesis 1,1-diacetates from aldehydes under solvent-free conditions

Aldehydes compounds selective converted to 1,1-diacetates as protective reagent with SiO2@FeSO4 nano composite as effective nano catalyst at room temperature under solvent-free condition and acetic anhydride (Ac2O) as acet

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.

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%).

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.

Zinc zirconium phosphate as an efficient catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions

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.

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.

Synthesis of 1,1-diacetates catalysed by silica-supported boron sulfonic acid under solvent-free conditions and ambient temperature

1,1-Diacetates derivatives were prepared using the direct condensation of aldehydes with acetic anhydride in the presence of silica-supported boron sulfonic acid (SiO2/B(SO4H)3) as a tri-functional inorganic Bronsted acid catalyst under solvent-free conditions at ambient temperature. The salient features of this methodology are: (i) cheaper process ready availability of the catalyst; (ii) versatility; (iii) high regio-selectivity of the procedure and recyclable property of the catalyst.

Sulfonated rice husk ash (RHA-SO3H): A highly powerful and efficient solid acid catalyst for the chemoselective preparation and deprotection of 1,1-diacetates

Rice husk ash (RHA), as a source of amorphous silica, was treated with chlorosulfonic acid and sulfonated rice husk ash (RHA-SO3H) as a highly powerful solid acid catalyst was obtained and characterized with a variety of techniques including IR, TGA, SEM, XRD, pH analysis, Hammett acidity function and BET method. This solid acid showed excellent catalytic activity for the protection and deprotection of aldehydes with Ac2O at room temperature under solvent free conditions. The procedure gave the products in excellent yields in very short reaction times and good to high yields. Also this catalyst can be reused for several times without loss of its catalytic activity.

Polystyrene-supported TiCl4 as a novel, efficient and reusable polymeric Lewis acid catalyst for the chemoselective synthesis and deprotection of 1,1-diacetates under eco-friendly conditions

Copolymer beads of styrene and divinylbenzene (5-7%) were synthesized and combined with titanium tetrachloride in CS2 to form a stable complex. The PS/TiCl4 complex was used as a mild and efficient polymer-supported Lewis acid catalyst for the preparation of 1,1-diacetates from various types of aldehydes under heterogeneous conditions at room temperature. Deprotection of the resulting 1,1-diacetates has also been achieved using the same catalyst in methanol. This new protocol has the advantages of easy availability, stability, reusability of the eco-friendly catalyst, high to excellent yields, chemoselectivity, simple experimental and work-up procedure. Moreover, this polymeric catalyst could be recovered easily and reused several times without significant loss in activity.

Chemoselective synthesis of geminal diacetates (acylals) using eco-friendly reusable propylsulfonic acid based nanosilica (SBA-15-Ph-PrSO3H) under solvent-free conditions

An expeditious method for the acetylation of aldehydes by mesoporous solid sulfonic acid (SBA-15-Ph-PrSO3H) under solvent-free reaction conditions was described. The route furnished selectively and in excellent yields the corresponding 1,1-diacetates starting from aldehydes and acetic anhydride using the environmentally friendly catalyst. The catalyst was found to be highly active and selective and could be recycled several times.