4316-37-4

Usage

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

Upstream product

• 64-17-5 ethanol 
• 24154-16-3 α,α‐dibromoethybenzene 
• 141-52-6 sodium ethanolate 
• 122-51-0 orthoformic acid triethyl ester 
• 98-86-2 acetophenone 
• 16694-46-5 ethyl formimidate hydrochloride 
• 536-74-3 phenylacetylene 
• 7647-01-0 hydrogenchloride 
• 5684-32-2 2-methyl-2-phenyl-[1,3]oxathiolane 
• 6230-62-2 (1-ethoxyvinyl)benzene 
• 2914-19-4 barium diethanolate 
• 100-52-7 benzaldehyde 
• 78-39-7 Triethyl orthoacetate 

Downstream Products

• 57818-33-4 N-ethyl-N-(1-phenylethenyl)aniline 
• 130597-97-6 (E)-4-(N,N-dimethylamino)-N-(1-phenylethylidene)aniline 
• 91132-84-2 (1-phenyl-ethylidene)-carbamic acid ethyl ester 
• 1144-20-3 2-phenyl-4-quinolinol 
• 15568-74-8 5-methyl-3-(4-nitro-phenyl)-5-phenyl-[1,4,2]dioxazole 
• 66329-11-1 <2-Aethoxy-styryl>-phosphonsaeure-dichlorid 
• 109482-03-3 (Z)-3-Phenyl-2-trimethylsilanylmethyl-but-2-enoic acid ethyl ester 
• 73007-56-4 <18O>acetophenone 
• 98-86-2 acetophenone 
• 91486-02-1 2-[1-(2-Amino-ethylsulfanyl)-1-phenyl-ethylsulfanyl]-ethylamine 
• 109773-81-1 (3Z)-4-ethoxy-1,1,1-trifluoro-4-phenylbut-3-en-2-one 
• 109773-82-2 (E)-1,1,1-Trichloro-4-ethoxy-4-phenyl-but-3-en-2-one 
• 6331-22-2 2-methyl-2-phenyl-[1,3]dithiane 
• 5769-02-8 2-methyl-2-phenyl[1,3]dithiolane 

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.

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.

A fluorinated cobalt(III) porphyrin complex for hydroalkoxylation of alkynes

A fluorinated cobalt(III) porphyrin complex [Co(TPFPP)-NTf2·2C2H5OH, where TPFPP=5,10,15,20-tetrakis(penta-fluorophenyl)porphyrin, Tf=CF3SO2] promotes hydroalkoxylation of alkynes to give acetals in good to excellent yields. The acetals can be directly functionalized with nucleophiles in a one-pot procedure.

A facile procedure for acetalization of aldehydes and ketones catalyzed by cerium(III) trifluoromethanesulfonate

Aldehydes and ketones are readily protected in the presence of trialkyl orthoformate and a catalytic amount of cerium(III) trifluoromethanesulfonate under mild conditions to give the corresponding acetals in good to excellent yields. Due to the mild reaction conditions, this method is compatible with acid-sensitive substrates. Copyright

Precursor and solvent effects in the nonhydrolytic synthesis of complex oxide nanoparticles for bioimaging applications by the ether elimination (Bradley) reaction

Investigation of the solvent and alkoxide precursor effect on the nonhydrolytic sol-gel synthesis of oxide nanoparticles by means of an ether elimination (Bradley) reaction indicates that the best crystallinity of the resulting oxide particles is achieved

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.

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.

Perchloric acid adsorbed on silica gel (HClO4-SiO2) as an inexpensive, extremely efficient, and reusable dual catalyst system for acetal/ketal formation and their deprotection to aldehydes/ketones

Perchloric acid adsorbed on silica gel (HClO4-SiO2) is reported as extremely efficient, inexpensive, and reusable catalyst for dual role for protection of aldehydes/ketones (with trialkyl orthoformates) as acetals/ketals and deprotection (with water-alcohol) to regenerate the carbonyl compounds in high yields at room temperature and in short times. Acetalization/ketalization of electrophilic aldehydes/ketones was carried out under solvent-free conditions. Weakly electrophilic aldehydes/ketones and aldehydes having a substituent that can coordinate with the catalyst, required the corresponding alcohol as solvent. Georg Thieme Verlag Stuttgart.

Pd(II)-catalyzed conversion of styrene derivatives to acetals: Impact of (-)-sparteine on regioselectivity

Pd[(-)-sparteine]Cl2 catalyzes the formation of dialkyl acetals from styrene derivatives with Markovnikov regioselectivity. The substrate scope of this reaction has been investigated, and initial mechanistic studies indicate that the reaction proceeds through an enol ether intermediate and a Pd-hydride.