772-01-0

Usage

Synthesis Reference(s)

Tetrahedron Letters, 16, p. 4543, 1975 DOI: 10.1016/S0040-4039(00)91066-9

InChI:InChI=1/C10H12O2/c1-2-5-9(6-3-1)10-11-7-4-8-12-10/h1-3,5-6,10H,4,7-8H2

Upstream product

• 75526-35-1 2-Phenyl-4H-[1,3]dioxin 
• 100-52-7 benzaldehyde 
• 504-63-2 trimethyleneglycol 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 776-88-5 5,5-dimethyl-2-phenyl-[1,3]dioxane 
• 78135-18-9 3-(1'-Methoxyphenoxy)-1-propanol 
• 103-67-3 benzyl-methyl-amine 
• 17887-80-8 1,3-bis(trimethylsiloxy)propane 
• 774-48-1 (diethoxymethyl)benzene 
• 17230-31-8 2-methoxy-1,3-dioxane 
• 5721-88-0 2-phenyl-1,3-oxathiolane 
• 5616-55-7 2-phenyl-1,3-dithiane 
• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 7334-52-3 benzaldehyde diethyldithioacetal 

Downstream Products

• 10601-29-3 5,5,7-Tris--8,8,8-trifluor-4,6-dioxa-octyl-benzoat 
• 942-95-0 3-chloropropyl benzoate 
• 67516-70-5 2-dichloromethyl-2-phenyl-[1,3]dioxane 
• 5695-78-3 2-chloromethyl-2-phenyl-[1,3]dioxane 
• 124062-30-2 2-[(3-Hydroxy-propoxy)-phenyl-methyl]-cyclohexanone 
• 124062-30-2 2-[(3-Hydroxy-propoxy)-phenyl-methyl]-cyclohexanone 
• 124389-41-9 3-(1-phenylbut-3-enyloxy)propan-1-ol 
• 124062-25-5 (1R,3S,4R)-3-[(S)-(3-Hydroxy-propoxy)-phenyl-methyl]-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 124062-26-6 (1R,3S,4R)-3-[(R)-(3-Hydroxy-propoxy)-phenyl-methyl]-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 776-88-5 5,5-dimethyl-2-phenyl-[1,3]dioxane 
• 133625-53-3 (1'RS)-1-<1'-(3''-Hydroxypropyloxy)-1'-phenylmethyl>uracil 
• 126006-59-5 2-Dibromomethyl-2-phenyl-[1,3]dioxane 
• 4799-68-2 3-benzyloxypropan-1-ol 
• 53088-81-6 1,3-bis(benzyloxy)propane 

Relevant academic research and scientific papers

An Intramolecular Iodine-Catalyzed C(sp3)?H Oxidation as a Versatile Tool for the Synthesis of Tetrahydrofurans

The formation of ubiquitous occurring tetrahydrofuran patterns has been extensively investigated in the 1960s as it was one of the first examples of a non-directed remote C?H activation. These approaches suffer from the use of toxic transition metals in overstoichiometric amounts. An attractive metal-free solution for transforming carbon-hydrogen bonds into carbon-oxygen bonds lies in applying economically and ecologically favorable iodine reagents. The presented method involves an intertwined catalytic cycle of a radical chain reaction and an iodine(I/III) redox couple by selectively activating a remote C(sp3)?H bond under visible-light irradiation. The reaction proceeds under mild reaction conditions, is operationally simple and tolerates many functional groups giving fast and easy access to different substituted tetrahydrofurans.

Phosphotungstic Acid Supported on Magnetic Mesoporous Tantalum Pentoxide Microspheres: Efficient Heterogeneous Catalysts for Acetalization of Benzaldehyde with Ethylene Glycol

Abstract: In this study, magnetically-recoverable core–shell catalysts with different amount of H3PW12O40 loading [Fe3O4@C@mTa2O5-NH2-PW12 (w%)] were prepared by the application of phosphotungstic acid supported on amino group functionalized magnetic core–shell mesoporous tantalum pentoxide microspheres. The prepared samples were characterized by FT-IR, N2-adsorption–desorption isotherms, TEM, SEM, Pyridine-IR analysis, XRD and magnetism. Fe3O4@C@mTa2O5-NH2-PW12 samples present both Br?nsted and Lewis acidity, large BET surface area and high magnetization. The catalytic activity was evaluated by the acetalization of different aldehydes with diols, and the results show that Fe3O4@C@mTa2O5-NH2-PW12 (14.47%) catalyst exhibits the highest catalytic activity for acetalization of aldehydes with glycols with 94.5% conversion of benzaldehyde and 99% selectivity to benzaldehyde glycol acetal at 80?°C. The catalytic activity of the catalyst for acetalization is related to its total acidity and Br?nsted–Lewis acid synergy. The catalyst Fe3O4@C@mTa2O5-NH2-PW12 can be easily recovered and reused for at least 5 times without obvious decrease of catalytic activity.

Direct anodic (thio)acetalization of aldehydes with alcohols (thiols) under neutral conditions, and computational insight into the electrochemical formation of the acetals

A versatile protocol for the production of acetals/thioacetals by means of direct electrochemical oxidation is developed here under neutral conditions, providing (thio)acetals with good functional group tolerance and a wide scope for both aldehydes and (thio)alcohols. DFT calculations reveal that direct electron transfer from the anode plays a key role in carbonyl activation during this acid free acetalization process.

A Direct Method for the Efficient Synthesis of Benzylidene Acetal at Room Temperature

For the first time, a metal-free direct method has been developed for the efficient synthesis of benzylidene acetal at room temperature using Dowex 50WX8 as a solid acid catalyst and Cl3CCN as a novel water scavenger. At room temperature, a wide variety of aryl and α,β-unsaturated aldehydes react readily with functionalized 1,2- and 1,3-diols to furnish the corresponding acetals in very good yields. Labile functional groups, like N-Boc, N-Cbz, -OTBDMS, -OBn, -N3 and acetonide are found to be stable under the reaction conditions. The versatility of this method is further demonstrated with carbohydrate substrates and optically active diols.

Robust acidic pseudo-ionic liquid catalyst with self-separation ability for esterification and acetalization

The novel acidic pseudo-ionic liquid catalyst with self-separation ability has been synthesized through the quaternization of triphenylphosphine and the acidification with silicotungstic acid. The pseudo-IL showed high activities for the esterification with average conversions over 90%. The pseudo-IL showed even higher activities for acetalization than traditional sulfuric acid. The homogeneous catalytic process benefited the mass transfer efficiency. The pseudo-IL separated from the reaction mixture automatically after reactions, which was superior to other IL catalysts. The high catalytic activities, easy reusability and high stability were the key properties of the novel catalyst, which hold great potential for green chemical processes.

Ce(III)-Based frameworks: From 1d chain to 3d porous metal-organic framework

The reaction of pyridine-2,4-dicarboxylic acid (2,4-H2 pydc) with Ce(NO3)36H2O, by applying only minor changes to the reaction conditions, generated a series of new one-, two-, and three-dimensional (1D, 2D, and 3D) coordination polymers, namely, [Ce(pydc)(Hpydc)(H2O)4]n (1), [Ce(pydc)(Hpydc)(H2O)2]n (2), and {[Ce3(pydc)4(H2O)2NO3]4H2O}n (3). The ancillary ligand interaction as well as the reaction conditions determine the specific coordination modes for the Hpydc- and pydc2- ligands and, in turn, discriminate between 1D, 2D, and 3D frameworks. Characterization of the prepared materials was performed using single-crystal and powder X-ray diffraction analysis, Fourier transform infrared spectroscopy, CHN elemental analysis, thermogravimetric analysis, and nitrogen adsorption/desorption techniques. Compound 1 consists of 1D chains, that compose of Ce3+ ions bridged by Hpydc- and pydc2- ligands, which further link via noncovalent interactions to form a 3D supramolecular architecture. Compound 2 assembles into 2D sheets with 1D channels. Similarly, via hydrogen-bonding interactions between two adjacent sheets, the 2D layers are further stacked into the final 3D supramolecular structure. Compound 3 is a 3D metal-organic framework (MOF), showing 1D helical channels. The progressive skeletal variation from the 1D chains (1) to 2D sheets (2) and 3D framework (3) is attributed to the flexibility of both the Ce(III) coordination sphere and coordination modes of the Hpydc- and pydc2- ligands under different reaction conditions. The three compounds illustrate how the tuning of the coordination geometry of Ce(III) translates into different dimensionality, which is readily influenced by reaction temperature and ancillary ligand presence. Moreover, the porosity of MOF 3 was confirmed by N2 and CO2 gas adsorption/desorption. Finally, the catalytic activity of MOF 3 was examined in acetalization reactions in a series of aromatic aldehydes with methanol.

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.

Graphene-catalyzed transacetalization under acid-free conditions

1,2- and 1,3-Diols are readily protected as cyclic acetals and ketals through a graphene-catalyzed transacetalization process. The methodology features an atom economic procedure since quasi-stoichiometric conditions have been developed. Unlike prior systems, the graphene-catalyzed transacetalization is performed under Br?nsted and Lewis acid-free conditions and without solvent. Our method has been applied to several volatile compounds that are unsuitable for complex work-up and extensive purification steps. The very unusual catalytic properties of graphene for transacetalization reactions are ascribed to molecular charge transfer between graphene and substrates.

A containing-SO 3 H acidic magnetic material catalytic preparing acetal (ketone) method

The invention discloses a method for preparing acetal (ketone) by catalyzing an acidic magnetic material containing -SO3H, which belongs to the technical field of chemical material and preparation thereof. According to the invention, mol ratio of aldehyde or ketone to alcohol used in the preparation method is 1: (1-5), mole of the acidic magnetic material catalyst accounts for 8-10% of that of the used aldehyde or ketone by calculating -SO3H, reaction temperature is 110 DEG C, the reaction time is 0.5-3 hours, the reaction pressure is one atmospheric pressure, a cooling step is carried out to room temperature after reaction is completed, the catalyst is sucked by a magnet, and the conversion rate, selectivity and acetal(ketone) yield of the reaction raw material are detected by a reaction solution through a gas chromatograph. Compared with the preparation method of other catalysts, the method has the advantages of high reaction selectivity, simple separation of the catalyst and the product, the catalyst enables cycle usage without any treatment, the operation of whole preparation process is simple, the economic benefit is high, and the method is convenient for industrial large scale production.

Acetals from primary alcohols with the use of tridentate proton responsive phosphinepyridonate iridium catalysts

The association of the new phosphinepyridonate ligands along with an iridium metallic precursor resulted in the selective acetalization of various primary alcohols via a formal dehydrogenative coupling reaction.