2186-92-7

Usage

Uses

Used in Pharmaceutical Industry:
P-ANISALDEHYDE DIMETHYL ACETAL is used as a precursor for the synthesis of various pharmaceutical compounds, such as 1-methoxy-1-(4-methoxyphenyl)hept-2-yne, 2,5-dioxopyrrolidin-1-yl-3-((4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane-4-carboxamido)propanoate, and 1-(p-anisyl)-2-(2-methoxyethyl)-3-phenylindene. These compounds have potential applications in the development of new drugs and therapies.
Used in Chemical Synthesis:
P-ANISALDEHYDE DIMETHYL ACETAL is used as a protecting group reagent for diols, particularly in the synthesis of carbohydrates. This application is crucial in the development of complex organic molecules and the protection of functional groups during chemical reactions.
Used in Flavor and Fragrance Industry:
P-ANISALDEHYDE DIMETHYL ACETAL is used as a flavor essence in the production of sunflower, cyclamen, and jasmine fragrances. Its unique properties contribute to the creation of distinct and appealing scents in the perfume and aromatherapy industries.
Used in Chemical Reactions:
P-ANISALDEHYDE DIMETHYL ACETAL is involved in allylation reactions with allyltrimethylsilane, catalyzed by Iron(III) chloride. This reaction is essential in the synthesis of various organic compounds and contributes to the development of new materials and products in the chemical industry.

InChI:InChI=1/C12H18O3/c1-4-14-12(15-5-2)10-6-8-11(13-3)9-7-10/h6-9,12H,4-5H2,1-3H3

Upstream product

• 2299-73-2 N,N-bis(4-methoxybenzylidene)hydrazine 
• 67-56-1 methanol 
• 140-67-0 Estragole 
• 616-42-2 dimethylsulfite 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-46-1 anethole 
• 637-69-4 4-Methoxystyrene 
• 824-94-2 p-methoxybenzyl chloride 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 124-41-4 sodium methylate 
• 104-93-8 p-methylanizole 
• 123-08-0 4-hydroxy-benzaldehyde 
• 1515-81-7 1-methoxy-4-(methoxymethyl)benzene 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 127721-50-0 1-Methoxy-1-(4-methoxy-phenyl)-4-phenyl-butan-2-ol 
• 4316-33-0 p-Methoxybenzoic acid methyl orthoester 
• 121-98-2 methyl 4-methoxybenzoate 
• 62370-08-5 methyl 4-tert-butoxybenzoate 
• 104865-85-2 trimethyl 4-tert-butoxyorthobenzoate 
• 17404-28-3 1-butyl-1-(4-methoxyphenyl)pentane 
• 124828-72-4 1-methoxy-4-(1-methoxyhept-2-yn-1-yl)benzene 
• 57056-44-7 H₂-5,15-di(p-methoxycarbonylphenyl)-10,20-di(p-tolyl)porphyrin 
• 57105-80-3 5,10,15-tris(4-methylphenyl)-20-(4-methoxycarbonylphenyl)porphyrin 
• 14527-51-6 5,10,15,20-tetra(p-tolyl)porphyrin 
• 131204-03-0 allyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside 
• 136520-23-5 Allyl-2-acetamido-2-desoxy-4,6-O-(4-methoxybenzyliden)-α-D-glucopyranosid 
• 134227-43-3 3-methoxy-3-(4-methoxyphenyl)-2-methyl-1-phenyl-1-propanone 
• 132924-96-0 4-methoxy-4-(4-methoxyphenyl)-2-butanone 

Relevant academic research and scientific papers

Microflow electroorganic synthesis without supporting electrolyte

Anodic methoxylation of several organic compounds has been successfully achieved in the absence of intentionally added supporting electrolyte using an electrochemical microflow system. The Royal Society of Chemistry 2005.

Microstructured reactor for electroorganic synthesis

In the present work a brief overview of microstructured devices, the advantages and disadvantages as well as the principles of a multiscale design approach are presented. The advantages mainly comprise uniform current density distribution, local control of the process parameters, high single-pass conversion of the reactant and reduced concentration of the supporting electrolyte needed to perform the reaction. The main challenge with this type of cell is gas evolution, a typical reaction taking place at the counter-electrode. The phenomena discussed are documented using the example of anodic methoxylation of 4-methylanisole. An analysis was made of the two-phase flow hydrodynamics inside the microstructured cell. The range of operational conditions suitable for the desired reaction was identified. The results were used together with the information on the electrode reaction kinetics in the form of the Butler-Volmer-type equation for the design of a suitable bipolar microstructured cell. A bipolar cell optimized to perform the desired reaction is reported. The results are compared with the published data. An analysis was performed that proved that the performance of the existing technology is more demanding in terms of energy consumption for the separation of the final product from the reaction mixture. The process intensification was evaluated on the basis of the available data.

Selective synthesis of 4,6-O-alkenylidene and -benzylidene acetals from unprotected sucrose by lanthanide(III) resin-catalyzed transacetalization

Lanthanide cation exchanged resins were used as catalysts for the acetalization of sucrose. Ytterbium(III)- and erbium(III)-exchanged resins promote the transacetalization of dialkyl acetals of α,β-unsaturated aldehydes. A two-step one-pot procedure provides direct access from the unsaturated aldehyde to a series of sucrose 4,6-acetals in good yields from unprotected sucrose without concomitant glycosidic bond cleavage.

MOF-808 as a recyclable catalyst for the photothermal acetalization of aromatic aldehydes

Metal-organic frameworks (MOFs) show promise for catalysis applications due to their porosity, high internal surface area, and structural adaptability. Typical acetylation reactions of aldehydes require elevated temperatures and excess alcohol to drive the reactions to completion. In this current work, MOF-808 is used as a heterogeneous catalyst for acetylation of aldehydes in methanol using a mild photothermal process. Optimized conditions gave 72% yield of 2-(dimethoxymethyl)naphthalene in the presence of 10 mol% MOF-808 at 45 °C using only a fluorescent lamp. MOF-808 can be recycled up to 5 times with no loss in catalytic activity. A proof-of-principle substrate scope demonstrates the potential utility for aromatic and aliphatic substrates.

Electro-Oxidative Selective Esterification of Methylarenes and Benzaldehydes

A mild and green electro-oxidative protocol to construct aromatic esters from methylarenes and alcohols is herein reported. Importantly, the reaction is free of metals, chemical oxidants, bases, acids, and operates at room temperature. Moreover, the design of the electrolyte was found critical for the oxidation state and structure of the coupling products, a rarely documented effect. This electro-oxidative coupling process also displays exceptional tolerance of many fragile easily oxidized functional groups such as hydroxy, aldehyde, olefin, alkyne, as well as neighboring benzylic positions. The enantiomeric enrichment of some chiral alcohols is moreover preserved during this electro-oxidative coupling reaction, making it overall a promising synthetic tool.

Thiol-initiated photocatalytic oxidative cleavage of the C=C bond in olefins and its extension to direct production of acetals from olefins

The oxidative cleavage of olefins to produce aldehydes/ketones is an important reaction in organic syntheses. In this manuscript, a mild and operationally simple protocol for the aerobic oxidation of olefins to produce carbonyl compounds was realized over ZnIn2S4under visible light, using air as the oxidant and a thiol as the initiator. It was proposed that the photogenerated holes over ZnIn2S4attack the thiol to produce thiyl radicals, which initiate the oxidative cleavage of the C=C bond in olefins to produce aldehydes/ketones. By further coupling with the condensation between the as-obtained aldehydes/ketones and alcohols, this strategy can also be applied to the production of different acetals directly from the olefins. This study demonstrates a new pathway to realize the oxidative cleavage of olefins to produce aldehydes/ketones, and also provides a new protocol for the production of acetals directly from the olefins.

Amino acid derivative, feed composition and application thereof

The invention provides an amino acid derivative, a feed composition and application thereof, and belongs to the technical field of animal feed additives. The amino acid derivative is a compound with astructure shown as a formula (I), and a stereoisomer, a tautomer, a solvate, a metabolite, a feed acceptable salt or a prodrug thereof. In formula (I) shown in the specification, Z is a C1-C3 alkylene group. X is an indole ring group with a structure shown as a formula (II). The formula (II) is shown in the specification, wherein Y is phenyl with the structure shown in the formula (III) shown inthe specification. The amino acid derivative is used as an animal feed additive, and can promote the growth of animals and improve the feed conversion.

Synthesis, structural determination and catalytic study of a new 2-D chloro-substituted zinc phosphate, (C8N2H20)[ZnCl(PO3(OH))]2

A novel chloro-substituted zinc-phosphate, (C8N2H20)[ZnCl(PO3(OH))], has been synthesized by a slow evaporation method in the presence of 1,3-cyclohexanebis- (methylamine), which acts as a template. The structure consists of vertex linked ZnO3Cl and PO3(OH) tetrahedral, assembled into corrugated porous layers [ZnCl(PO3(OH))2]∞ with (4.82) topology. The optical properties were also investigated using Diffuse Reflecting Spectroscopy (DRS), showing that the title compound has semiconducting properties. In addition, the catalytic activity of (C8N2H20)[ZnCl(PO3(OH))]2 has been tested in the acetalisation reaction of aldehydes. The title compound displayed a high catalytic activity with practically total conversion in many examples using MeOD as solvent and as the sole source of acetalisation. More importantly, the reaction crudes are very clean and only the preferred products are found in the NMR spectra.

Chemoenzymatic Synthesis of 5-Hydroxymethylfurfural (HMF)-Derived Plasticizers by Coupling HMF Reduction with Enzymatic Esterification

Biobased plasticizers, as substitutes for phthalates, have been synthesized from 5-hydroxymethylfurfural (HMF) and carboxylic acids (or esters) through a chemoenzymatic cascade process that involves as its first step the reduction of 5-hydroxymethylfurfural into 2,5-bis(hydroxymethyl)furan (BHMF), followed by the esterification of BHMF with carboxylic acids (or esters) by using a supported lipase (Novozym 435). The reduction of HMF into BHMF is performed by using monodisperse metallic Co nanoparticles with a thin carbon shell (Co@C) with high activity and selectivity. After optimization of reaction conditions (temperature, hydrogen pressure, and solvent), it is possible to achieve 97 % conversion of HMF with 99 % selectivity to BHMF after 2 h reaction time. The reduction of HMF and esterification of BHMF using carboxylic acids or vinyl esters as acyl donors by lipase are optimized separately in batch and in fixed-bed continuous reactors. The coupling of two flow reactors (for reduction and subsequent esterification) working under optimized reaction conditions affords the diesters of BHMF in roughly 90 % yield with no loss of activity during 60 h of operation.

Synthesis of (E)-α,β-unsaturated carboxylic esters derivatives from cyanoacetic acid via promiscuous enzyme-promoted cascade esterification/Knoevenagel reaction

A new enzymatic protocol based on lipase-catalyzed cascade toward (E)-α,β-unsaturated carboxylic esters is presented. The proposed methodology consists of elementary organic processes starting from acetals and cyanoacetic acid leading to the formation of desired products in a cascade sequence. The combination of enzyme promiscuous abilities gives a new opportunity to synthesize complex molecules in the one-pot procedure. Results of studies on the influence of an enzyme type, solvent, and temperature on the cascade reaction course are reported. The presented methodology provides meaningful qualities such as significantly simplified process, excellent E-selectivity of obtained products and recycling of a biocatalyst.