2403-61-4

Usage

Synthesis Reference(s)

Synthesis, p. 330, 1984 DOI: 10.1055/s-1984-30832Tetrahedron Letters, 23, p. 1537, 1982 DOI: 10.1016/S0040-4039(00)87152-X

InChI:InChI=1/C11H15ClO2/c1-3-13-11(14-4-2)9-5-7-10(12)8-6-9/h5-8,11H,3-4H2,1-2H3

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 64-17-5 ethanol 
• 873376-62-6 triethoxyantimony 
• 122-51-0 orthoformic acid triethyl ester 
• 97-93-8 triethylaluminum 
• 67-56-1 methanol 
• 3510-48-3 4-chlorobenzaldehyde azine 
• 33598-76-4 1-chloro-4-(ethoxymethyl)benzene 

Downstream Products

• 39512-66-8 (4-chloro-benzylidene)-[1,2,4]oxadiazol-3-yl-amine 
• 92832-15-0 α,α-bis(2-hydroxy-6-isopropyl-tropon-3yl)-4-chlorotoluene 
• 104-88-1 4-chlorobenzaldehyde 
• 64-17-5 ethanol 
• 3157-65-1 N-(p-chlorobenzylidene)-p-toluenesulfonamide 
• 36382-28-2 1-Chloro-4-(1,3,3-triethoxy-propyl)-benzene 
• 92594-57-5 α-ethoxy-p-chlorobenzylphosphonic acid diethyl ester 
• 33210-79-6 1-Chloro-4-(chloro-ethoxy-methyl)-benzene 
• 6302-92-7 1-(bis(ethylthio)methyl)-4-chlorobenzene 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 69900-95-4 2-(p-toluenesulfonyl)-3-(p-chlorophenyl)oxaziridine 
• 878274-47-6 C₂₅H₂₃ClO 
• 878274-51-2 C₂₇H₂₇ClO₃ 

Relevant academic research and scientific papers

Practical acetalization and transacetalization of carbonyl compounds catalyzed by recyclable PVP-I

A novel PVP-I catalyzed acetalizations/transacetalizations of carbonyl compounds has been developed processing with a mild and easy handling fashion. Different types of Acyclic and cyclic acetals were prepared from carbonyl compounds or their acetals successfully. Further applications of newly developed catalytic combination were testified. This protocol featured with simplicity of operation, mild reaction condition, short reaction time, recyclable of catalyst and broad substrates scope with excellent yields.

A facile and efficient protocol for esterification and acetalization in a PEG1000-D(A)IL/toluene thermoregulated catalyst-media combined systems

A novel efficient and recyclable temperature-dependent biphasic catalyst and reaction media combined system comprised of PEG-1000 linked dicationic acidic ionic liquid and toluene was developed and applied in esterification of aromatic acids and acetalization of aromatic aldehydes with good to excellent yields. This system is characteristic of temperature-dependent reversible biphasic property, simple and facile recyclability, high catalytic activity and extensive substrate and reaction adaptability.

Bis(perfluorooctanesulfonyl)imide supported on fluorous silica gel: Application to protection of carbonyls

The immobilization of bis(perfluorooctanesulfonyl)imide (HNPf2) on fluorous silica gel (FSG) and its utilization in protection of carbonyls have been investigated. This system is reasonably general and can be applied to converting several carbonyls to the corresponding acetals and ketals in good to excellent yields. There is no need for the use of anhydrous solvents or inert atmosphere. Recycling studies have shown that the FSG-supported HNPf2 catalyst can be readily recovered and reused several times without significant loss of activity.

Single-step conversion of electron-deficient aldehydes into the corresponding esters in aqueous alcohols in the presence of iodine and sodium nitrite

The direct conversion of aldehydes into their corresponding esters in the presence of iodine and sodium nitrite in aqueous alcohols is reported. In all these reactions, alcohol serves as reactant and also as reaction medium. Almost quantitative yields were obtained with aldehydes containing electron-withdrawing substituents and heterocyclic aldehydes. Georg Thieme Verlag Stuttgart.

Cobalt(II) schiff base functionalized mesoporous silica as an efficient and recyclable chemoselective acetalization catalyst

Cobalt(II) Schiff base functionalized mesoporous silica was synthesized from covalent attachment via the introduction of Co(OAc)2 to salicylaldimine functionalized mesoporous silica. The catalyst proved to be chemoselective one for the acetalization of aldehydes to the corresponding acetals in alcohol. The immobilized catalyst can be easily recovered and reused for at least ten reaction cycles without significant loss of its catalytic activity.

Gallium triiodide as a highly efficient and mild catalyst for the diethyl acetalization of carbonyl compounds

Diethyl acetals were obtained from carbonyl compounds in good to excellent yields under mild reaction conditions in the presence of triethyl orthoformate and a catalytic amount of gallium triiodide in anhydrous ethanol.

Nucleophilic phosphine-catalyzed [3+2] cycloaddition of allenes with N-(thio)phosphoryl imines and acidic methanolysis of adducts N-(thio)phosphoryl 3-pyrrolines: a facile synthesis of free amine 3-pyrrolines

In this report, the dipolarophile imines with easily removable activating group O,O-diethyl(thio)phosphoryl have been investigated in the nucleophilic phosphine-catalyzed [3+2] cycloaddition reaction of electron-deficient allenes. Under the catalysis of a tertiary phosphine, N-(thio)phosphorylimines readily undergo the [3+2] cycloaddition reaction with ethyl 2,3-butadienoate or ethyl 2,3-pentadienoate, affording the corresponding N-(thio)phosphoryl 3-pyrrolines in moderate to high yields with good diastereoselectivity. Removal of the (thio)phosphoryl group from the adducts has been successfully achieved via the acidic methanolysis of the P-N bond, giving the free amine 3-pyrrolines in fair to good yields without severe aromatization. Thus, a facile synthesis of N-unsubstituted 3-pyrrolines is established from the phosphine-catalyzed [3+2] cycloaddition reaction of allenes with imines.

Iron(III) tosylate in the preparation of dimethyl and diethyl acetals from ketones and β-keto enol ethers from cyclic β-diketones

An efficient method for conversion of ketones to their corresponding dimethyl and diethyl acetals and of cyclic β-diketones into β-keto enol ethers using Fe(OTs)3 as a catalyst is described. Copyright Taylor & Francis Group, LLC.

Acid-free, organocatalytic acetalization

The acid-free, organocatalytic acetalization of various aldehydes and ketones with N,N′-bis[3,5-bis(trifluoromethyl)phenyl]thiourea is presented. The neutral, double hydrogen bonding thiourea catalyst can be used at very low loadings of 0.01-1 mol% at room temperature to furnish the respective acetals in 65-99% yield at turnover frequencies around 600 h-1. Acid-labile TBDMS-protected as well as unsaturated aldehydes can be converted efficiently into their acetals utilizing this very mild and highly practical method.

Bronsted acidic ionic liquids as efficient and recyclable catalysts for protection of carbonyls to acetals and ketals under mild conditions

A series of acidic ionic liquids have been used as efficient catalysts for the protection of various carbonyl compounds at room temperature. The features of mild conditions, satisfactory isolated yield, simple workup, and the recyclability of the catalyst were present in this process. Copyright Taylor & Francis, Inc.