2403-59-0

Usage

Uses

Used in Polymer and Coating Production:
p-(diethoxymethyl)toluene is utilized as a crosslinking agent in the manufacturing process of polymers and coatings. Its role in this application is to enhance the structural integrity and durability of the final products by forming covalent bonds between polymer chains.
Used in Fragrance Production:
In the fragrance industry, p-(diethoxymethyl)toluene serves as an intermediate. It contributes to the creation of various scent profiles by participating in chemical reactions that produce the desired aromatic compounds.
Used in Pharmaceutical Synthesis:
p-(diethoxymethyl)toluene is also employed as an intermediate in the synthesis of pharmaceuticals. Its chemical properties make it a valuable component in the development of new drugs, aiding in the formation of complex molecular structures that can have therapeutic effects.

InChI:InChI=1/C12H18O2/c1-4-13-12(14-5-2)11-8-6-10(3)7-9-11/h6-9,12H,4-5H2,1-3H3

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 122-51-0 orthoformic acid triethyl ester 
• 88920-26-7 ethoxy-p-methylphenylacetic acid 
• 64-17-5 ethanol 
• 18584-23-1 hydroxy-p-tolyl-acetic acid ethyl ester 
• 998-30-1 Triethoxysilane 
• 3395-83-3 4-methylbenzaldehyde dimethylacetal 

Downstream Products

• 86657-73-0 1-Methyl-4-(1,3,3-triethoxy-propyl)-benzene 
• 92594-53-1 diethyl (ethoxy(p-tolyl)methyl)phosphonate 
• 180399-95-5 [1-p-Tolyl-meth-(E)-ylidene]-phosphoramidic acid diethyl ester 
• 35368-01-5 α-chloro-p-methylbenzyl ethyl ether 
• 56637-44-6 2-(4-methylphenyl)-1,3-dithiane 
• 106-42-3 para-xylene 
• 951762-81-5 (E)-N-(4-methylbenzylidene)-4-nitrobenzenesulfonamide 
• 92832-10-5 3-(α-ethoxy-4-methylbenzyl)-6-isopropyltropolone 
• 945491-88-3 N-4-methylbenzylidene-O,O-diethylthiophosphoramide 
• 945491-96-3 N-4-methylbenzylidene-diphenylthiophosphinamide 
• 878274-49-8 C₂₈H₃₀O₃ 
• 1188448-08-9 8,8-dimethyl-2,2-diphenyl-3-p-tolyl-2,8-dihydrocyclopenta[a]indene 
• 64-17-5 ethanol 
• 104-87-0 4-methyl-benzaldehyde 

Relevant academic research and scientific papers

Tungsten hexachloride (WCl6), a highly efficient and chemoselective catalyst for acetalization of carbonyl compounds

Various types of aldehydes and ketones could be converted chemoselectively to their corresponding 1,3-dioxanes or diethyl acetals in the presence of catalytic amounts of tungsten hexachloride (WCl6) in good to excellent yields in CH2Cl2 or under neat conditions, respectively.

Conjugate addition of acetal-derived benzyl radicals generated from low-valent titanium-mediated CO bond cleavage

A new method for the generation of benzyl radicals from acetals via low-valent titanium-mediated homolytic CO bond cleavage is presented. The low cost and availability of the developed titanium reagent enable efficient access to α-alkoxy carbon radical species via the developed reaction.

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.

Formation of Acetals and Ketals from Carbonyl Compounds: A New and Highly Efficient Method Inspired by Cationic Palladium

The development of a new, highly efficient, and simple method for masking carbonyl groups as acetals and ketals is described. This methodology relies on the nature of the palladium catalyst to direct the acetalization/ketalization reaction. This new protocol is mild and proceed with a very low catalyst loading at ambient temperatures. The method has been extended to a wide variety of different carbonyl compounds with various steric encumbrances to form the corresponding acetals and ketals in excellent yields.

Antimony(v) catalyzed acetalisation of aldehydes: An efficient, solvent-free, and recyclable process

A highly selective, solvent-free process for the acetalisation of aldehydes was achieved by the use of a readily accessible antimony(v) catalyst which we previously prepared in our lab as a tetraarylstibonium triflate salt ([1][OTf]). High yields of the acetals were achieved in the presence of stoichimetric amounts of either triethoxymethane or triethoxysilane. It was found that triethoxymethane reactions required longer time to reach completion when compared to triethoxysilane reactions which were completed upon mixing of the reagents. The products can be easily separated from the catalyst by distillation which enabled further use of [1][OTf] in additional calytic reactions (up to 6 cycles). Moreover, [1]+ also catalyzed the deprotection of the acetals into their corresponding aldehydes using only water as a solvent.

Tropylium salts as efficient organic Lewis acid catalysts for acetalization and transacetalization reactions in batch and flow

Acetalization reactions play significant roles in the synthetically important masking chemistry of carbonyl compounds. Herein we demonstrate for the first time that tropylium salts can act as organic Lewis acid catalysts to facilitate acetalization and transacetalization reactions of a wide range of aldehyde substrates. This metal-free method works efficiently in both batch and flow conditions, prompting further future applications of tropylium organocatalysts in green synthesis.

Direct conversion of acetals to esters with high regioselectivity via O,P-acetals

A new direct conversion of O,O-acetals to esters via O,P-acetal intermediates was developed. The regioselective cleavage of unsymmetrical cyclic acetals occurred to give the more crowded esters as single isomers.

Tetrafluoroboric acid adsorbed on silica gel as a reusable heterogeneous dual-purpose catalyst for conversion of aldehydes/ketones into acetals/ketals and back again

Aldehydes and ketones can be protected as acetals and ketals by treatment with trimethyl orthoformate (TMOF) or triethyl orthoformate (TEOF) under the catalytic influence of tetrafluoroboric acid adsorbed on silica gel (HBF 4-SiO2). In the case of aldehydes or ketones with highly electrophilic carbonyl group, the reactions are carried out under solvent-free conditions. Aryl alkyl ketones, aryl styryl ketones, aldehydes with weakly electrophilic carbonyl groups, and aldehydes with substituents that can coordinate with the catalyst require the presence of the corresponding alcohol as solvent. For substrates that can be converted into acetals under neat conditions, the acetal formation takes place at a faster rate when the alcohol is used as the solvent. The catalyst can be recovered and reused/recycled four times (after reactivation after each use) without any significant decrease in its catalytic efficiency. The parent aldehydes/ketones are regenerated from the corresponding acetals/ketals in high yields by the treatment with water-alcohol in the presence of HBF4-SiO2 at room temperature for short times. Excellent selectivity was observed during inter- and intramolecular competition studies involving carbonyl substrates with varying electronic and steric environments. Selective acetal formation of benzaldehyde takes place in the presence of 4-(dimethylamino)benzaldehyde, thiophene-2-carboxaldehyde, 1-naphthaldehyde, 9-anthraldehyde, or acetophenone, but 3-nitrobenzaldehyde undergoes selective acetal formation in preference to benzaldehyde. In the case of 4-acetylbenzaldehyde, exclusive acetal formation of the aldehyde carbonyl group occurs. Georg Thieme Verlag Stuttgart.

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.