Method for alcoxyphenol and alcoxyhydroxybenzaldehyde production

FIELD: chemistry.

SUBSTANCE: method for alkoxyphenol production comprises O-alkylation of at least one hydroxyphenol to form at least one alkoxyphenol, at that, the said reaction is carried out using an O-alkylating agent, an aqueous solvent containing a Bronsted base and an organic solvent with a base/O-alkylating agent ration in the range of 0.5 to 1.5 moles of base per mole of O-alkylating agent, with an O-alkylating agent/hydroxyphenol ratio in the range of 0.5 to 2 moles of O-alkylating agent per mole of hydroxyphenol and with an organic solvent/hydroxyphenol ratio of less than 280 ml, preferably in the range of 10 to 250 ml and more preferably in the range of 50 to 150 ml of an organic solvent per mole of hydroxyphenol. One of the versions of the alkoxyhydroxybenzaldehyde production method comprises preparation of alkoxyphenol from hydroxyphenol by the foregoing method and a reaction of the aldehyde group addition to the resulting alkoxyphenol to obtain the corresponding alkoxyhydroxybenzaldehyde, preferably by condensation reaction between alkoxyphenol and glyoxylic acid, followed by oxidation of the resulting compound.

EFFECT: proposed method for alkoxyphenol production allows the desired product to be obtained in good yield and high purity with high conversion of initial hydroxyphenol.

11 cl, 3 dwg, 7 ex

 



 

Same patents:

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to novel compounds of formula III or to its pharmaceutically acceptable salts, in which: R1 and R2 are independently selected from group, consisting of: (a) H, (b) (C2-C6)alkyl, (c) C1-C6 alkyl, interrupted by one or more groups -O-, (d) (C0-C3)alkyl-(C3-C7)cycloalkyl and (e) (CH2)nQ, where n=1-2 and where Q stands for aromatic ring system, which has from 5 to 6 ring atoms C, and Q can be independently substituted with groups up to 3 in number, selected from halogen, on condition that R1 and R2 simultaneously do not stand for H, and each alkyl of R1 and R2 can be independently substituted with one or more groups, selected from group, consisting of halogen, hydroxy, cyano, CF3 or C1-C4 alkyl, or R1 and R2 together with carbon, to which they are attached, form 3-7-member cycloalkyl or 6-member heterocycloalkyl ring, including one oxygen atom and which in case of necessity carries C1-C4 alkyl substituent, or R1 and R2 together with carbon, to which they are connected, form 3-7-member cycloalkyl ring, substituted with R20 and R21, and R20 and R21 together with carbon or carbons, to which they are connected, form 3-7-member cycloalkyl ring; R6 stands for C1-C6 alkyl; each R7 independently stands for C1-C6 alkyl; Y stands for -O-; R4 is selected from group, consisting of: (a) (C0-C3)alkyl-(C3-C7)cycloalkyl, (b) trifluoroethyl, and (c) trifluoropropyl; Z stands for phenyl or bicyclic ring system, which has 9 ring atoms, independently selected from C, N, O and S, on condition that not more than 3 ring atoms in any single ring differs from C, and said ring system can carry to 3 substituents, independently selected from group, consisting of R6, CF3 and SR6; and R5 is selected from group, consisting of NO2, NH2, F, Cl, Br, CN, SR6, S(O)2N(R7)2 and (C1-C4)alkyl, and each alkyl can be independently substituted with one or more halogens or CF3. Invention also relates to pharmaceutical composition for treatment of neurodegenerative disorder or improvement of cognitive function, containing therapeutically effective quantity of said compound; as well as to method of treatment of neurodegenerative disorder, for instance Alzheimer's disease, or improvement of cognitive function.

EFFECT: compounds act as modulators of gamma-secretase.

31 cl, 14 tbl, 3147 ex, 1 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method for asymmetrical hydrogenation, catalysed by transition metals, acrylic acid derivatives of formula (I), in which R1 denotes H or optionally substituted C1-C20-alkyl, C5-C20-aryl or C5-C20-heteroryl radical, R2 denotes optionally substituted C1-C20-alkyl, C5-C20-aryl or C5-C20-heteroaryl radical, and R3 denotes H or C1-C6-alkyl radical, which involves hydrogenation of compounds of formula (I), optionally in a solvent, in the presence of one or more hydrogen donors, using a catalyst system which contains a transition metal selected from ruthenium, rhodium and iridium and a combination of a chiral phosphoric ligand of formula (II), in which Cn, together with two oxygen atoms and a phosphorus atom, form an optionally substituted ring, having 2-6 carbon atoms, and R4 denotes an optionally substituted alkyl, aryl, alkoxy- or aryloxy-radical or a NR5R6 group in which R5 and R6 can be independently hydrogen or optionally substituted alkyl, aryl, aralkyl or alkaryl radical, or together with a nitrogen atom can form a ring, and an achiral phosphinic ligand of formula (III), in which R is optionally substituted alkyl or aryl radical, to obtain corresponding compounds of formula (IV) in which each R1, R2 and R3 are as described above. Formula (I), Formula (II), Formula P(R)3 (III), Formula (IV).

EFFECT: improved method for asymmetrical hydrogenation.

20 cl, 3 tbl, 29 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to novel derivatives of carboxylic acid represented by the general formula (I): , their pharmaceutically acceptable salts or esters wherein values Y, L, X, T, Z, M, R1, W and are given in the invention claim. Proposed compounds possess insulin-sensitizing effect and they are double agonists with respect to PPARα and γ, and triple agonists with respect to PPARα, β(δ) and γ. Except for, the invention relates to a medicinal agent and pharmaceutical compositions based on the claimed derivatives of carboxylic acid, to methods for prophylaxis or treatment of diseases, and to using derivatives carboxylic acid for preparing a medicinal agent.

EFFECT: valuable medicinal properties of compounds and pharmaceutical compositions.

56 cl, 2 tbl, 609 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to novel intermediate compounds and inmproved method for synthesis of compound of the formula (C): . Proposed method is based on using inexpensive parent substances and provides synthesis of intermediate compounds with the high yield and high purity degree being without carrying out procedures for chromatographic purification and can be realized in large-scale industry manufacture. Invention relates to improved methods for synthesis of compound of the formula (I): , compound of the formula (II): , compound of the formula (III): , compound of the formula (VIII): , compound of the formula (IX): , and to a reagent consisting of boron tribromide and 2,6-dimethylpyridine. Method is used for a sparing and selective splitting a methyl group in aromatic methyl ethers.

EFFECT: improved method of synthesis.

12 cl, 8 ex

The invention relates to an improved method for producing a p-hydroxymandelic compounds by condensation in the water, in the presence of an alkaline agent, an aromatic compound containing at least one hydroxyl group and having a free parapolitica, with Glyoxylic acid

The invention relates to new bicyclic aromatic compounds of General formula (I) having the ability to bind RXRand pharmaceutical compositions based on them, which can be used in medicine, veterinary medicine and in cosmetics

The invention relates to a new process for the preparation of 2,2-dimethyl-5-(2,5-dimethylphenoxy)-pentanol acid of the formula (I)

OCOOH

(I) This connection is used for regulating the level of blood lipids

FIELD: chemistry.

SUBSTANCE: invention relates to a method of obtaining highly fluorinated carboxylic acids and their salts, as well as substances-precursors, which includes an impact on a highly fluorinated olefin, which has the general formula (I): Rf-(O)n-(CF2)m-CF=CF2 of a formic acid derivative in accordance with the general formula (II): HCOR in the presence of a radical initiator to form a substance-precursor of carboxylic acid in the form of O-ethers, S-ethers or an amide adduct of the general formula (III): Rf-(O)n-(CF2)m-CFH-CF2-COO and, optionally, in case of an acid obtaining, hydrolysis of an adduct of formula (III) to form carboxylic acid or its salts with the general formula (IV): Rf-(O)n-(CF2)m-CFH-CF2-COO-M+, where in formulas (II) and (III) R represents a residue O-M+, S-M+, OR' or SR' or NR'R", where R' and R" are independent on each other linear or branched or cyclic aliphatic residues, which contain at least one carbon atom and which do not have an alpha-H-atom, where the alpha-H-atom represents a hydrogen atom, bond with a carbon atom, bound with O, S or N in groups OR', SR' or NR'R", and where in formulas (I), (III), (IV) Rf represents H, either a perfluorinated or fluorinated linear or branched alkyl residue which can contain one or several catenary oxygen atoms, and n constitutes 1 or 0, m represents a number from 0 to 6, and M+ represents a cation.

EFFECT: method makes it possible to obtain target compounds with the high output.

8 cl, 7 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a novel method of producing 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid of formula (I) through a Suzuki reaction between 3-adamantyl-4-methoxyphenylcarboxylic acid of formula (II) and 6-bromo-2-naphthoic acid of formula (III), wherein the reaction between compounds (II) and (III) is carried out at temperature between 60 and 110C for between 30 minutes and 24 hours in an inert gas atmosphere in the presence of a palladium catalyst and a base in a polar solvent, followed by treatment with an acid. The invention also relates to use of compounds of formulae (II) and (III) to produce a compound of formula (I).

EFFECT: single-step method enables to obtain desired product with high output.

13 cl, 2 dwg, 3 ex

FIELD: chemistry.

SUBSTANCE: invention relates to production of anionic surfactants, specifically to methods of producing carboxymethylates of oxyethylated alkylphenols used as components of detergents for domestic and industrial purposes - intensification of oil extraction processes by increasing ratio of extraction of oil from oil deposits. The method of producing oxyethylated alkylphenol-based anionic surfactants is realised through condensation of oxyethylated alkylphenols with sodium monochloroacetate in molar ratio 1.0:(0.8-1.0) in nitrogen medium while heating in the presence of an alkaline agent at 45-50C. The alkaline agent used is crystalline potassium hydroxide taken in molar ratio to the oxyethylated alkylphenol equal to (0.7-1.0):1.0 or its mixture with crystalline sodium hydroxide in the same molar ratio to the oxyethylated alkylphenol. After condensation, a hydrogen ion concentration (pH) regulator is added to the reaction mixture in molar ratio of pH regulator to the oxyethylated alkylphenol equal to (0.01-0.1):1.0 until attaining pH of the reaction mixture of 8.0-9.0. The anionic surfactant is stored without partial decomposition and resin formation for not less than 100 days.

EFFECT: efficient method of producing anionic surfactants.

4 cl, 1 tbl, 15 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to novel intermediate compounds and inmproved method for synthesis of compound of the formula (C): . Proposed method is based on using inexpensive parent substances and provides synthesis of intermediate compounds with the high yield and high purity degree being without carrying out procedures for chromatographic purification and can be realized in large-scale industry manufacture. Invention relates to improved methods for synthesis of compound of the formula (I): , compound of the formula (II): , compound of the formula (III): , compound of the formula (VIII): , compound of the formula (IX): , and to a reagent consisting of boron tribromide and 2,6-dimethylpyridine. Method is used for a sparing and selective splitting a methyl group in aromatic methyl ethers.

EFFECT: improved method of synthesis.

12 cl, 8 ex

The invention relates to an improved method for producing a p-hydroxymandelic compounds by condensation in the water, in the presence of an alkaline agent, an aromatic compound containing at least one hydroxyl group and having a free parapolitica, with Glyoxylic acid

FIELD: chemistry.

SUBSTANCE: method consists in air oxygen oxidation of lignin, obtained by fermentative hydrolysis of wood of coniferous species or wood, affected by brown or mottled rot, with content of lignin 40-90 wt % in water-alkali medium at higher temperatures and pressure. The process is carried out in presence of catalysts on the basis of copper hydroxide with continuous supply of alkali solution into reactor for 1-150 minutes.

EFFECT: method makes it possible to reduce alkali consumption counted per a kilo of obtained vanillin, and consumption of fermentative lignin, which reduces amount of organic substance, formed as byproducts, in sewage water and improves ecological compatibility of the process.

10 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of purifying vanillin obtained from lignin oxidation products, by reacting vinillin-containing extracts with aqueous solutions sodium bisulphite, followed by decomposition of the vanillin-bisulphite derivative. The method is characterised by that the vanillin-bisulphite derivative is heated in an autoclave to 120-170C, the vapour-gas phase is released and vanillin is extracted from the obtained mixture or solution, followed by recycling the obtained aqueous solution of sulphurous anhydride and sodium sulphate into a solution of sodium bisulphite.

EFFECT: method enables to avoid the use of sulphuric acid and alkali when purifying vanillin, widely used in food, perfume, cosmetic and pharmaceutical industry.

5 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to a method of separating vanillin, which is widely used in food, perfume-cosmetic and pharmaceutical industries, from lignin oxidation products by reacting vanillin-containing extracts with aqueous sodium hydrosulphite NaHSO3 solutions. The solutions used have sodium hydrosulphite concentration of 320-400 g/l and the vanillin-hydrosulphite derivative formed is separated from excess sodium hydrosulphite solution in form of a precipitate by filtration, centrifuging or decantation.

EFFECT: method enables to cut consumption of sodium hydrosulphite and increases the distribution ratio of vanillin into the precipitate and aqueous phase from the organic phase, which reduces the volume of extracts and re-extracts when separating vanillin.

3 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of extracting ortho-vanilin and iso-vanilin from aqueous solutions. The method involves addition of a salting-out agent - sodium chloride to aqueous solutions of ortho-vanilin and iso-vanilin and a solution of polyvinyl caprolactam prepared beforehand, having concentration of 5-15 wt % until achieving 34-35 wt % content of salt in the solution, with volume ratio of the aqueous phase to organic phase equal to 10:1. The organic phase is extracted and separated, analysed spectrophotometrically and the recovery ratio (R, %) of ortho-vanilin and iso-vanilin is calculated using the formula: R=D100/(D+r), where D is coefficient of distribution of ortho-vanilin and iso-vanilin between the solution of polyvinyl caprolactam and the aqueous solution, r is the ratio of equilibrium volumes of the aqueous and organic phases.

EFFECT: method increases recovery ratio of ortho-vanilin and iso-vanilin from aqueous solutions.

1 tbl, 2 ex

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