3674-77-9

Usage

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 4605, 1996 DOI: 10.1016/0040-4039(96)00888-X

InChI:InChI=1/C10H12O2/c1-10(11-7-8-12-10)9-5-3-2-4-6-9/h2-6H,7-8H2,1H3

Upstream product

• 107-21-1 ethylene glycol 
• 98-86-2 acetophenone 
• 4316-35-2 acetophenone dimethyl acetal 
• 108-86-1 bromobenzene 
• 764-48-7 ethyleneglycol vinyl ether 
• 2916-31-6 2,2-dimethyl-1,3-dioxolane 
• 5684-32-2 2-methyl-2-phenyl-[1,3]oxathiolane 
• 67-56-1 methanol 
• 36881-02-4 2-(4-chlorophenyl)-2-methyl-1,3-dioxolane 
• 109-92-2 ethyl vinyl ether 
• 75-89-8 2,2,2-trifluoroethanol 
• 116-11-0 2-Methoxypropene 
• 19073-15-5 2-(4-nitrophenyl)-2-methyl-1,3-dioxolane 
• 917-54-4 methyllithium 

Downstream Products

• 854840-71-4 3-methyl-3-phenyl-[1,4]dioxanecarboxylic acid ethyl ester 
• 3418-21-1 2-(bromomethyl)-2-phenyl-1,3-dioxolane 
• 4799-66-0 2-(1-phenylethoxy)ethanol 
• 939-55-9 2-chloroethyl benzoate 
• 98-83-9 isopropenylbenzene 
• 6331-22-2 2-methyl-2-phenyl-[1,3]dithiane 
• 2040-37-1 benzyl 1-phenylethyl ether 
• 98-85-1 1-Phenylethanol 
• 7381-30-8 2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane 
• 26305-99-7 1-iodo-2-trimethylsilyloxy-ethane 
• 4743-74-2 2-phenylpent-4-en-2-ol 
• 599-67-7 1,1-diphenylethanol 
• 1015002-36-4 4-ethyl-2-phenyloctan-2-ol 
• 878-57-9 2-methyl-2-phenyl-[1,3]dioxane 

Relevant academic research and scientific papers

Selective Acetalization of ethylene glycol with methyl 2-napthyl ketone over solid acids: Efficacy of acidic clay supported Cs2.5H0.5PW12O40

Catalytic conversion of biomass to value added products is relevant with regard to several industries. Biomass derived ethylene glycol has many applications. Acetalization is used to synthesize valuable chemicals and also occasionally to protect carbonyl

Experimental and Theoretical Study of the Effectiveness and Stability of Gold(I) Catalysts Used in the Synthesis of Cyclic Acetals

Different [AuL]+ fragments (L = tertiary phosphines, ylides, or NHC carbene) have been tested under mild conditions as suitable catalysts for the transformation of terminal or internal alkynes into the corresponding cyclic acetals upon reaction

Ni-catalyzed reductive decyanation of nitriles with ethanol as the reductant

A nickel-catalyzed reductive decyanation of aromatic nitriles has been developed, in which the readily available and abundant ethanol was applied as the hydride donor. Various functional groups on the aromatic rings, such as alkoxyl, amino, imino and amide, were compatible in this catalytic protocol. Heteroaryl, benzylic and alkenyl nitriles were also tolerated. Mechanistic investigation indicated that ethanol provided hydride efficientlyviaβ-hydride elimination in this reductive decyanation.

Green efficient synthesis of ketal under catalysis of ionic liquid TTPT

The invention discloses a method for green efficient synthesis of ketal under catalysis of ionic liquid TTPT. The method comprises the following steps: adding TTPT and a water-carrying agent into a raw material I and a raw material II, and carrying out a heating reflux reaction for 110-150 minutes, wherein R1 and R2 in formulas I and II are independently selected from a group consisting of a methyl group, an ethyl group and a phenyl group, or R1 and R2 are connected and cyclized to form a 5-to-10-membered naphthenic base; and R3 is selected from H or-OH. Compared with the prior art, the catalytic yield of the TTPT is remarkably improved, a good catalytic effect is achieved, and experimental operation is easy and convenient.

Utilization of 1,3-Dioxolanes in the Synthesis of α-branched Alkyl and Aryl 9-[2-(Phosphonomethoxy)Ethyl]Purines and Study of the Influence of α-branched Substitution for Potential Biological Activity

Syntheses of α-branched alkyl and aryl substituted 9-[2-(phosphonomethoxy)ethyl]purines from substituted 1,3-dioxolanes have been developed. Key synthetic precursors, α-substituted dialkyl [(2-hydroxyethoxy)methyl]phosphonates were prepared via Lewis acid mediated cleavage of 1,3-dioxolanes followed by reaction with dialkyl or trialkyl phosphites. The best preparative yields were achieved under conditions utilizing tin tetrachloride as Lewis acid and triisopropyl phosphite. Attachment of purine bases to dialkyl [(2-hydroxyethoxy)methyl]phosphonates was performed by Mitsunobu reaction. Final α-branched 9-[2-(phosphonomethoxy)ethyl]purines were tested for antiviral, cytostatic and antiparasitic activity, the latter one determined as inhibitory activity towards Plasmodium falciparum enzyme hypoxanthine-guanine-xanthine phosphoribosyltransfesase. In most cases biological activity was only marginal.

METHOD FOR PRODUCTION OF AROMATIC COMPOUND

PROBLEM TO BE SOLVED: To solve such problems that the replacement of a nitro group with a hydrogen atom in production of an aromatic compound requires two-type reactions different from each other comprising reduction to an amino group and conversion of diazonium salt, and those procedures contain such problems that many processes are required and it takes time in production in view of convenience in aftertreatment of reaction and refining operation; and further, a careful handling is required regarding the diazonium salt because that salt is unstable depending on the type of compound and is an intermediate having sometimes the risk of explosion. SOLUTION: There is provided an aromatic compound production method characterized by including: reacting an aromatic nitro compound with a proton supply compound under the presence of a metal catalyst; and directly reducing the nitro group of the aromatic nitro compound to a hydrogen atom. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Reductive Denitration of Nitroarenes

The Pd-catalyzed reductive denitration of nitroarenes has been achieved via a direct cleavage of the C-NO2 bonds. The catalytic conditions reported exhibit a broad substrate scope and good functional-group compatibility. Notably, the use of inexpensive propan-2-ol as a mild reductant suppresses the competitive formation of anilines, which are normally formed by other conventional reductions. Mechanistic studies have revealed that alcohols serve as efficient hydride donors in this reaction, possibly through β-hydride elimination from palladium alkoxides.

8-Hydroxy-2-methylquinoline-modified H4SiW12O40: A reusable heterogeneous catalyst for acetal/ketal formation

A heteropoly acid based organic hybrid heterogeneous catalyst, HMQ-STW, was prepared by combining 8-hydroxy-2-methylquinoline (HMQ) with Keggin-structured H4SiW12O40 (STW). The catalyst was characterized via elemental analysis, X-ray diffractometry (XRD), Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), thermogravimetric analysis (TG) and potentiometric titration analysis. The catalytic performance of the catalyst was assessed in the ketalization of ketones with glycol or 1,2-propylene glycol. Various reaction parameters, such as the glycol to cyclohexanone molar ratio, catalyst dosage, reaction temperature and time, were systematically examined. HMQ-STW exhibited a relatively high yield of corresponding ketal, with 100% selectivity under the optimized reaction conditions. Moreover, catalytic recycling tests demonstrated that the heterogeneous catalyst exhibited high potential for reusability, and it was revealed that the organic modifier HMQ plays an important role in the formation of a heterogeneous system and the improvement of structural stability. These results indicated that the HMQ-STW catalyst is a promising new type of heterogeneous acid catalyst for the ketalization of ketones.

Synthesis of dioxolanes and oxazolidines by silica gel catalysis

Abstract: Ethylene glycol condensed with carbonyl compounds in the presence of silica gel or alumina, without solvent and under pressure, affords 1,3-dioxolanes. 2-Amino-2-methylpropanol also condensed with carbonyl compounds in the presence of silica gel or an acid-activated clay, without solvent and under pressure, produces oxazolidines. To explain these results, we propose that the glycol and the aminopropanol react with Br?nsted (H+) and Lewis acid sites (Si and Al) located on the surface of the catalysts, leading to the products via various ionic intermediates.

Ketalization of ketones to 1,3-dioxolanes and concurring self-aldolization catalyzed by an amorphous, hydrophilic SiO2-SO3H catalyst under microwave irradiation

The amorphous, mesoporous SiO2-SO3H catalyst with a surface area of 115 m2 g-1 and 1.32 mmol H+ per g was very efficient for the protonation of ketones on a 10percent (m/m) basis, and the catalyst-bound intermediates can be trapped by polyalcohols to produce ketals in high yields or suffer aldol condensations within minutes under low-power microwave irradiation. The same catalyst can easily reverse the ketalization reaction. Printed in Brazil-