58378-32-8

Upstream product

• 67-56-1 methanol 
• 529-20-4 2-methylphenyl aldehyde 
• 70380-66-4 2-chlorobenzaldehyde dimethyl acetal 
• 74-88-4 methyl iodide 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 138622-40-9 cis-2-o-tolyl-4-chloro-tetrahydropyran 
• 91466-65-8 1-Isopropyl-2,2-dimethyl-3-o-tolyl-aziridine 
• 91-20-3 naphthalene 
• 91466-68-1 C₁₆H₁₈O 
• 91548-27-5 C₁₆H₁₈O 
• 91548-28-6 C₁₆H₁₈O 
• 91466-70-5 (1S,2S)-2-Butyl-1-methoxy-1,2,3,4-tetrahydro-naphthalene 
• 91466-71-6 (1S,3S)-3-Butyl-1-methoxy-1,2,3,4-tetrahydro-naphthalene 
• 91466-72-7 (1S,3R)-3-Butyl-1-methoxy-1,2,3,4-tetrahydro-naphthalene 
• 176858-00-7 C₁₅H₁₄N₂O₂S 
• 141376-09-2 ((4S,5S)-5-Dimethylaminomethyl-2-o-tolyl-[1,3]dioxolan-4-ylmethyl)-dimethyl-amine 
• 78315-43-2 1-[(butylthio)methyl]-2-methyl-benzene 
• 1374030-80-4 (1-methoxy-3-phenylprop-2-yn-1-yl)-2-methylbenzene 
• 1374030-60-0 C₁₇H₁₈O₂ 

Relevant academic research and scientific papers

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.

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.

Multicomponent Aromatic and Benzylic Mannich Reactions through C?H Bond Activation

Multicomponent Mannich reactions through C?H bond activation are described. These transformations allowed for the straightforward generation of densely substituted benzylic and homo-benzylic amines in good yields. The reaction involves a reaction between two transient species: an organometallic species, generated by transition-metal-catalyzed sp2 or sp3 C?H bond activation and an in situ generated imine. The use of an acetal as an aldehyde surrogate was found essential for the reaction to proceed. The process could be successfully applied to RhIII-catalyzed sp2 C?H bond functionalization and extended to CuII-catalyzed sp3 C?H bond functionalization.

Silver-Catalyzed Olefination of Acetals and Ketals with Diazoesters to β-Alkoxyacrylates

The first silver-catalyzed reaction of acetals or ketals with diazoesters leading to trisubstituted or tetrasubstituted β-alkoxyacrylates is now reported. A broad range of acetals and ketals bearing different substituents is compatible with this protocol and thus provides an attractive approach for the synthesis of complex β-alkoxyacrylates. The power of this method was further demonstrated by the successful synthesis of picoxystrobin, which is one of the most popular agricultural fungicides commercialized by Dupont.

Method for preparing alkoxy acrylate

The invention discloses a method for preparing an alkoxy acrylate. The method comprises that diazo ester and substituted acetal or ketal as raw materials undergo an alkenylation reaction in the presence of Lewis acid as a catalyst at 50-120 DEG C for 1-24h, then the solvent is drained through pumping and the product is subjected to column chromatography separation so that the alkoxy acrylate compound is obtained. The reaction raw materials and the catalyst are easily available and cheap, the synthesis process is simple, the synthesis cost is greatly reduced, the reaction conditions are mild, the yield is high, the industrialization is easy, the reaction raw materials and the catalyst are clean and non-toxic, and the environmental pollution is small.

House bulb light-induced photochemical acetalization of carbonyl compounds catalyzed by Eosin Y

We have systematically studied the reactions of acetalization and found that high reaction efficiency can be achieved using cheap and readily available organic Eosin Y as catalyst. The reaction proceeds smoothly under house bulbs and shows excellent functional group tolerance. The substrates of the reaction system are compatible with aromatic aldehydes, aliphatic aldehydes, aromatic ketones, and cyclic ketones with high yields.

Acid-catalyzed highly diastereoselective and effective synthesis of 1,3-disubstituted tetrahydropyrano[3,4-b]indoles

We successfully explored for the first time that trifluoroacetic acid (TFA) can effectively catalyze the oxa-Pictet-Spengler reaction of secondary tryptophols and acetals to synthesize 1,3-disubstituted 1,3,4,9-tetrahydropyrano[3,4-b]indoles in high yield (up to >99%) and diastereoselectivity (>20:1). The secondary tryptophols were synthesized from indole-3-acetic acid. The one-pot synthesis of tetrahydropyrano[3,4-b]indoles was successfully developed from secondary tryptophols and in situ prepared acetals from aldehydes and trimethylorthoformate and thus the cost-efficiency of the protocol was effectively enhanced. Finally, the catalytic asymmetric synthesis of the 1,3-disubstituted tetrahydropyrano[3,4-b]indole was also demonstrated after enantioselective achievement of highly enantiopure secondary tryptophols.

Direct Asymmetric Friedel-Crafts Reaction of Naphthols with Acetals Catalyzed by Chiral Bronsted Acids

The Friedel-Crafts method synthesis of chiral ethers from various acetals and naphthols catalyzed by chiral Bronsted acids with acetic acid as an effective additive is described. We found that the chiral phosphoric acid (R)-TRIP could efficiently catalyze the asymmetric Friedel-Crafts reaction of naphthols with acetals affording chiral ethers in good enantioselectivity and yield.

A General Access to Propargylic Ethers through Br?nsted Acid Catalyzed Alkynylation of Acetals and Ketals with Trifluoroborates

A general Br?nsted acid catalyzed methodology for the alkynylation of acetals and ketals with alkynyltrifluoroborate salts has been developed. The reaction proceeds rapidly to afford valuable synthetic building block propargylic ethers in good to excellent yields. Unlike Lewis acid catalyzed transformations of trifluoroborates, this approach does not proceed via unstable organodifluoroborane intermediate. As a result, the developed methodology features excellent functional group tolerance and good atom economy. Br?nsted acid catalyzed alkynylation of acetals and ketals is described. Alkynyltrifluoroborate salts react rapidly to afford propargylic ethers. Organodifluoroborane, which is a common intermediate in Lewis acid catalyzed reactions of trifluoroborates, has not been observed. The reaction exhibits generally high yields and excellent functional group tolerance.

Efficient enantioselective synthesis of dihydropyrans using a chiral N, N ′-dioxide as organocatalyst

The bifunctional organocatalyst C3 N,N′-dioxide has been successfully applied to the asymmetric cascade Michael/hemiacetalization reaction of α-substituted cyano ketones and β,γ-unsaturated α-ketoesters for the synthesis of multifunctionalized chiral dihydropyrans. The corresponding products were obtained in excellent yields (up to 99%) with high to excellent enantioselectivities (up to 99% ee).