58378-33-9

Usage

Uses

1-(Dimethoxymethyl)-2-methoxybenzene is used as a reagent in the chemical industry for the preparation of acyclic and semicyclic O/O acetals. These acetals are important intermediates in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Chemical Synthesis:
In the chemical synthesis industry, 1-(Dimethoxymethyl)-2-methoxybenzene is used as a key building block for the creation of complex organic molecules. Its unique structure allows for selective functionalization and modification, making it a valuable tool in the development of new compounds with specific properties and applications.
Used in Pharmaceutical Research:
In the pharmaceutical industry, DMMB may be employed as a starting material or intermediate in the synthesis of novel drug candidates. Its versatility in chemical reactions enables the development of new molecules with potential therapeutic applications, such as those targeting specific diseases or conditions.
Used in Flavor and Fragrance Industry:
Due to its pleasant aromatic properties, 1-(Dimethoxymethyl)-2-methoxybenzene can also be used in the flavor and fragrance industry as a component in the creation of various scents and flavors. Its unique aroma profile can contribute to the development of new and innovative products in this sector.

Upstream product

• 135-02-4 ortho-anisaldehyde 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 
• 90-02-8 salicylaldehyde 
• 612-15-7 o-methoxystyrene 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 124-41-4 sodium methylate 

Downstream Products

• 138622-39-6 (2R*,4S*)-4-chloro-2-(2-methoxyphenyl)tetrahydro-2H-pyran 
• 137105-49-8 [Methoxy-(2-methoxy-phenyl)-methyl]-phosphonic acid diethyl ester 
• 137105-57-8 (6,7-Dimethoxy-2H-thiochromen-4-yl)-(2-hydroxy-phenyl)-methanone 
• 137105-56-7 6,7-dimethoxy-4-(o-methoxybenzoyl)-2H-thiochromene 
• 137105-51-2 1-(2,2-Diethoxy-ethylsulfanyl)-4,5-dimethoxy-2-[(Z)-2-methoxy-2-(2-methoxy-phenyl)-vinyl]-benzene 
• 195254-01-4 benzyl 2-benzyloxycarbonylamino-2-deoxy-4,6-O-(R)-(2-methoxybenzylidene)-α-D-glucopyranoside 
• 130652-11-8 meso-1,2-bis-(2'-methoxyphenyl)-1,2-dimethoxyethane 
• 130652-11-8 d,l-1,2-bis-(2'-methoxyphenyl)-1,2-dimethoxyethane 
• 217320-69-9 2-[hydroxy(4-methoxyphenyl)methyl]cyclohexane-1-one 
• 61924-58-1 ethyl 3-(2-methoxyphenyl)-2-nitroacrylate 
• 61924-68-3 ethyl 3-(2-methoxyphenyl)-2-nitropropanoate 

Relevant academic research and scientific papers

Chemoselective Nucleophilic Functionalizations of Aromatic Aldehydes and Acetals via Pyridinium Salt Intermediates

The development of a novel chemoselective functionalization can diversify the strategy for synthesizing the target molecules. The perfect chemoselectivity between aromatic and aliphatic aldehydes is difficult to achieve by the previous methods. The aromatic aldehyde-selective nucleophilic addition in the presence of aliphatic aldehydes was newly accomplished. Namely, the aromatic aldehyde-selective nucleophilic addition using arenes and allyl silanes proceeded in the presence of trialkylsilyl triflate and 2,2′-bipyridyl, while the aliphatic aldehydes completely remained unchanged. The reactive pyridinium-type salt intermediate derived from an aromatic aldehyde chemoselectively underwent the nucleophilic substitution. Moreover, the aromatic acetals as the protected aldehydes could be directly transformed into similar pyridinium salt intermediates, which reacted with various nucleophiles coexisting with the aliphatic aldehydes.

Unique chemoselective Mukaiyama aldol reaction of silyl enol diazoacetate with aldehydes and acetals catalyzed by MgI2 etherate

Functionalized diazo acetoacetates are prepared by an efficient Mukaiyama aldol reaction between 3-TBSO-2-diazo-3-butenoate with aldehydes and acetals under mild reaction conditions. A variety of substituted aldehydes and the corresponding acetals are both accessible in good to excellent yields through this methodology. MgI2 etherate (MgI2·(OEt2)n) is the preferred catalyst and, the addition proceeds without decomposition of the diazo moiety. In addition, this MgI2·(OEt2)n-catalyzed Mukaiyama aldol reaction shows unique chemoselectivity towards aldehydes and acetals.

Ru(II)-functionalized SBA-15 as highly chemoselective, acid free and sustainable heterogeneous catalyst for acetalization of aldehydes and ketones

Combining electron deficient Ru(II) coordination sites with organofunctionalized SBA-15, (L)Ru(II)@SBA-15, result in a mild, neutral, water scavenger free and chemo-selective acetalization catalyst for cyclic/acyclic acetals. Vacant coordination sites of ruthenium in (L)Ru(II)@SBA-15 activates protecting groups as well as reactants simultaneously and restricts the reverse acetalization reaction. Synthesized (L)Ru(II)@SBA-15 catalyst has been thoroughly characterized and act as competitive catalyst compared to conventional acid catalysts. (L)Ru(II)@SBA-15 performs high catalytic activity as well as selectivity within 20 min with high TOF. The catalyst can be recycled and reaction parameters are optimized.

Preparation of acetals from aldehydes and alcohols under basic conditions

A new, simple protocol for the synthesis of acetals under basic conditions from non-enolizable aldehydes and alcohols has been reported. Such reactivity is facilitated by a sodium alkoxide along with a corresponding trifluoroacetate ester, utilizing formation of sodium trifluoroacetate as a driving force for acetal formation. The usefulness of this protocol is demonstrated by its orthogonality with various acid-sensitive protecting groups and by good compatibility with functional groups, delivering synthetically useful acetals complementarily to the synthesis under acidic conditions from aldehydes and alcohols.

Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions

We report here on the use of ethyl nitroacetate as a glycine template to produce α-amino esters. This started with a study of its condensation with various arylacetals to give ethyl 3-aryl-2-nitroacrylates followed by a reduction (NaBH4 and then zinc/HCl) into α-amino esters. The scope of this method was explored as well as an alternative with arylacylals instead. We also focused on various [2 + 3] cycloadditions, one leading to a spiroacetal, which led to the undesired ethyl 5-(benzamidomethyl)isoxazole-3-carboxylate. The addition of ethyl nitroacetate on a 5-methylene-4,5-dihydrooxazole using cerium(IV) ammonium nitrate was also explored and the synthesis of other oxazole-bearing α-amino esters was achieved using gold(I) chemistry.

Phosphorylated Polyacrylonitrile Fibers as an Efficient and Greener Acetalization Catalyst

A novel solid acid catalyst (PANEAPF) is developed by immobilization of phosphoric acid on polyacrylonitrile fiber through covalent bonding. Various characterization techniques such as elemental analysis (EA), X-ray photoelectron spectroscopy (XPS), Fourier transform infrared spectroscopy (FTIR), etc. are utilized to confirm the successful grafting and the stability of the fiber catalysts during application. PANEAPF shows high catalytic activity in the acetalization of aldehydes owing to the high utilization efficiency of its functionalized acid sites. In addition, the strong polarity micro-environment in the surface layers of PANEAPF make it highly suitable for catalytic application in both water and alcohol. Furthermore, the fiber catalyst can be applied to the acetalization of aldehydes in a continuous-flow process at room temperature, and shows excellent reactivity and superior recyclability (over 20 times). The many advantages of PANEAPF such as simple preparation, convenient regulation of acid amount, high durability, and eco-friendly process make it very attractive for fixed-bed reactors in the chemical industry.

Photochemical Approaches to the Bilobalide Core

Bilobalide is a tetracyclic sesquiterpene containing three contiguous γ-lactone rings and an unusual tert-butyl group, which is found in the leaves of the ginkgo tree (Ginkgo biloba). Three different photochemical approaches towards bilobalide's unique sk

Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides

A new substrate class for nickel-catalyzed C(sp3) cross-coupling reactions is reported. α-Oxy radicals generated from benzylic acetals, TMSCl, and a mild reductant can participate in chemoselective cross-coupling with aryl iodides using a 2,6-bis(N-pyrazolyl)pyridine (bpp)/Ni catalyst. The mild, base-free conditions are tolerant of a variety of functional groups on both partners, thus representing an attractive C-C bond-forming approach to dialkyl ether synthesis. Characterization of a [(bpp)NiCl] complex relevant to the proposed catalytic cycle is also described.

The asymmetric Cu(ii)-indolinylmethanol complex catalyzed Diels-Alder reaction of 2-vinylindoles with β,γ-unsaturated α-ketoesters: An efficient route to functionalized tetrahydrocarbazoles

An efficient asymmetric Diels-Alder reaction of 2-vinylindoles with β,γ-unsaturated α-ketoesters has been developed for the construction of functionalized tetrahydrocarbazoles. The products were obtained in high yields (up to 96%) with good stereoselectiv