51673-84-8

Usage

Uses

Glyoxal dimethyl acetal is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuffs.

Synthesis Reference(s)

Synthetic Communications, 18, p. 1343, 1988 DOI: 10.1080/00397918808078802

General Description

This product is a 60wt% solution of 2,2-dimethoxyacetaldehyde (glyoxal dimethyl acetal) in water. The aldol condensation of 2,2-dimethoxyacetaldehyde with acetoacetic ester in the absence of the catalyst and solvent has been reported. It participates in the synthesis of isoxazoline vinyl ester pseudopeptides and tetrahydro-β-carboline derivatives of barbituric acid analogs.

InChI:InChI=1/C4H8O3/c1-6-4(3-5)7-2/h3-4H,1-2H3

Upstream product

• 21962-24-3 1,1-dimethoxy-2-butene 
• 67-56-1 methanol 
• 131543-46-9 Glyoxal 
• 30934-97-5 2,2-dimethoxyethanol 
• 106-24-1 Geraniol 
• 97-97-2 chloroacetaldehyde dimethyl acetal 
• 1071116-48-7 geranyl oxyacetaldehyde dimethyl acetal 
• 5370-08-1 1,1,4,4-tetramethoxy-2-butene 
• 6044-68-4 3,3-dimethoxyprop-1-ene 

Downstream Products

• 114736-26-4 (Z)-4,4-Dimethoxy-but-2-enoic acid ethyl ester 
• 19255-60-8 (E)-4,4-dimethoxy-but-2-enoic acid ethyl ester 
• 118264-83-8 N-dodecyl N-(dimethoxy-2,2) ethylidene imine 
• 78771-58-1 N-Benzhydryl-3,3-dimethoxy-2-(2-oxo-azetidin-1-yl)-propionamide 
• 166413-85-0 N-(1-acetyl-5-indolinyl)-2,2-dimethoxyethylamine 
• 161681-84-1 2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester 
• 205192-94-5 N-[(2,2-dimethoxyethyl)amino]-4-(2-propyl)aniline 
• 212200-24-3 4-Dimethoxymethyl-2-methyl-6-phenyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 170691-24-4 N-<3-<2-(dimethylamino)ethoxy>-4-methoxyphenyl>aminoacetaldehyde dimethyl acetal 
• 439148-93-3 4-(4-fluoro-phenyl)-5-(2-methylsulfanyl-pyrimidin-4-yl)-1H-imidazole-2-carbaldehyde 
• 218162-49-3 2-dimethoxymethyl-4-(4-fluorophenyl)-5-(2-methylsulfanylpyrimidin-4-yl)-1H-imidazole 
• 406954-90-3 (2,2-dimethoxyethyl)-[2-(2-bromophenyl)ethyl]amine 
• 573970-34-0 (R,R)-(-)-bis(α-methylbenzyl)aminoacetaldehyde dimethyl acetal 

Relevant academic research and scientific papers

Preparation method of 2, 2-dimethoxyacetaldehyde

The invention discloses a preparation method of 1, 2-dimethoxyacetaldehyde. Hydroxyacetaldehyde is adopted as a raw material and a methanol raw material, S2O8 /Zn-MCM-41 solid superacid is adopted as a catalyst, the acidity is high and 2, 2-methoxyethanol can be obtained with high selectivity, then 2, 2-methoxyacetaldehyde is obtained under the action of an oxidizing agent, the product is easy to separate, and the purity of dimethoxyacetaldehyde reaches up to 95% or above.

A two-step process for the synthesis of hydroxytyrosol

A new process for the synthesis of hydroxytyrosol (3,4-dihy-droxyphenylethanol), the most powerful natural antioxidant currently known, by means of a two-step approach is reported. Catechol is first reacted with 2,2-dimethoxyacetaldehyde in basic aqueous medium to produce the corresponding mandelic derivative with > 90 % conversion of the limiting reactant and about 70 % selectivity to the desired para-hydroxyalkylat-ed compound. Thereafter, the intermediate is hydrogenated to hydroxytyrosol by using a Pd/C catalyst, with total conversion of the mandelic derivative and 68 % selectivity. This two-step process is the first example of a synthetic pathway for hydroxytyrosol that does not involve the use of halogenated components or reduction methodologies that produce stoichiometric waste. It also avoids the complex procedure currently used for hydroxytyrosol purification when it is extracted from wastewa-ter of olive oil production.

A atorvastatin sandbank calcium chiral synthesis of intermediates method

The invention discloses a synthesis method for a chiral intermediate of atorvastatin calcium, and belongs to the technical field of medical intermediate synthesis. The synthesis method is characterized in that according to the process route, not only are dangerous, highly toxic and expensive chemicals such as butyl lithium, editpotassium cyanide and periodic acid in chemical synthesis prevented from being used, but also an ee value of the chiral intermediate is effectively improved due to usage of a mixed chiral catalysts of titanium iso-propylate and S-xenol. According to the synthesis method, the raw materials are low in cost and easy to obtain, the route operation is easy, the repeatability is good, the yield is very high, and the synthesis method is suitable for industrial production.

Synthesis method of rosuvastatin calcium key chiral intermediate

The invention discloses a synthesis method of a rosuvastatin calcium key chiral intermediate and belongs to the technical field of synthesis of medical intermediates. According to the technical scheme, the method is characterized as the specification. With the adoption of the process route, use of an expensive medicine, namely, ethyl (R)-4-bromo-3-hydroxybutyrate, is avoided, the ee (enantiomeric excess) value of a product is effectively increased due to use of a chiral catalyst, raw materials of the synthesis method are simple and easy to obtain, the route is simple to operate, the repeatability is good, the yield is very high, and the method is suitable for industrial production.

Fructose-6-phosphate aldolases as versatile biocatalysts for nitrocyclitol syntheses

Efficient and stereoselective polyhydroxylated nitrocyclitol syntheses were performed via biocatalysed aldol reactions. The key step was based on a one-pot/one-enzyme cascade reaction process where two reactions occur: aldolase-catalysed aldolisation and spontaneous intramolecular nitroaldolisation. The synthetic methodology was investigated using fructose-6-phosphate aldolase A129S for the synthesis of known nitrocyclitols. Improvements were obtained which involved less steps and increased yields. Several new nitrocyclitols were also prepared using hydroxyacetone (HA) as the donor and FSA wt. From nitrocyclitol stereochemical analyses, the intramolecular nitro-Henry reaction stereoselectivity was dependent on the donor substrate used, HA or dihydroxyacetone (DHA). Whereas DHA provided two stereoisomers, four were obtained using HA.

Metal-free, mild, nonepimerizing, chemo- and enantio- or diastereoselective N-alkylation of amines by alcohols via oxidation/imine-iminium formation/reductive amination: A pragmatic synthesis of octahydropyrazinopyridoindoles and higher ring analogues

A mild step and atom-economical nonepimerizing chemo- and enantioselective N-alkylating procedure has been developed via oxidation/imine-iminium formation/reduction cascade using TEMPO-BAIB-HEH-Bronsted acid catalysis in DMPU as solvent and a stoichiometric amount of amine. The optimized conditions were further extended for the nonenzymatic kinetic resolution of the chiral amine thus formed under nonenzymatic in situ hydrogen-transfer conditions using VAPOL-derived phosphoric acid (VAPOL-PA) as the Bronsted acid catalyst. The enantioselective cascade of the presented reaction was successfully utilized in the synthesis of octahydropyrazinopyridoindole and its higher ring analogues.

Process for the separation, by countercurrentwise liquid-liquid extraction, of a glyoxal diacetal from a crude mixture comprising it

The invention relates to a method for separating a diacetal of the glyoxal of a raw mixture comprising said diacetal of the glyoxal and a monoacetal of the glyoxal, by means of counter-current liquid-liquid extraction.

METHOD FOR PROCESSING COMPOSITIONS CONTAINING 1,1,2,2-TETRAMETHOXYETHANE AND GLYOXAL DIMETHYL ACETAL

Disclosed is a method for processing an aqueous composition containing 1,1,2,2-tetramethoxyethane, glyoxal dimethyl acetal, and methanol by means of distillation. Said method is characterized in that the composition is processed in a partition column so as to form low-boiling, medium-boiling, and high-boiling fractions. A partition is disposed in the longitudinal direction of the partition column such that a common top column area, a common bottom column area, a feeding zone comprising a rectification section and a stripping section, and a removing zone encompassing a stripping section and a rectification section are created. The aqueous composition is delivered to the central area of the feeding zone.

Process for continuously preparing acetals of alpha, beta-dicarbonyl compounds

The present invention relates to a process for preparing acetals of α,β-dicarbonyl compounds of the general formula (R″O)2CRCR′(OR″)2 which are obtained by continuous reaction of α,β-dicarbonyl compounds R—CO—CO—R′ with alcohols R″OH or HO—X—OH in countercurrent.

Process for the continuous preparation of acetals of alpha,beta-dicarbonyl compounds

The production of linear and cyclic acetals of formulae (I) and (Ia) respectively comprises reacting alpha ,beta -dicarbonyl compounds (II) of the type R-CO-CO-R' with alcohols (III) of the type ROH or HO-X-OH continuously in countercurrent apparatus: (RO)2CRCR'(OR)2 (I). The production of linear acetals (I) and cyclic acetals (Ia) comprises reacting alpha ,beta -dicarbonyl compounds, selected from glyoxal and higher dialdehydes, diketones and ketoaldehydes with 1-8 carbon (C) alkyl, 3-8 C cycloalkyl, 2-8 C alkenyl, 2-8 C alkynyl and/or 6-18 C aryl groups, with 1-8 C alkanols, 3-8 C cycloalkanols, 2-8 C alkenols, 2-8 C alkynols or diols with a 2-12 C alk(en)ylene chain continuously in a countercurrent apparatus. [Image] R and R' : H, 1-8 C alkyl, 3-8 C cycloalkyl, 2-8 C alkenyl, 2-8 C alkynyl or 6-18 C aryl R : 1-8 C alkyl, 3-8 C cycloalkyl, 2-8 C alkenyl or 2-8 C alkynyl or a chain X; and X : 2-12 C alkylene or 2-12 C alkenylene linking both O atoms of the alpha -C atom and/or both O atoms of the beta -C atom.