Method for producing 1-adamantyl acetaldehyde

FIELD: chemistry.

SUBSTANCE: present invention relates to the method of producing 1-adamantyl-acetaldehyde, used as a valuable intermediate product for synthesis of bioactive substances and functional organic materials. The method comprises a catalytic reaction between 1-adamantanol and vinyl acetate as an unsaturated compound. Vinyl acetate, 2.5-fold molar excess relative to 1-adamantanol; the reaction is caried out for 2 hours in dichloroethane at dichloroethane boiling point, indium tribromide is used as a catalyst, 5 mole %.

EFFECT: target product produced using a simple process and readily available raw materials.

2 tbl, 1 ex

 



 

Same patents:

The invention relates to the chemistry of adamantane derivatives, and in particular to a new method of obtaining-adamantylidene aldehydes of General formula

where R1=H, R2=CH3WITH3H7WITH4H9; R1=R2=CH3,which are intermediates for the synthesis of biologically active substances, using the adamantane derivative

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing a compound of formula , where Z is optionally substituted phenyl and Q is phenyl or 1-naphthalenyl, each optionally substituted. The method involves distillation of water from a mixture containing a compound of formula , a compound of formula , a base containing at least one compound selected from a group comprising alkali-earth metal hydroxides of formula 4 M(OH)2, where M is Ca, Sr or Ba, alkali metal carbonates of formula 4a (M1)2CO3 , where M1 is Li, Na or K, 1,5-diazabicyclo[4,3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene, and an aprotic solvent capable of forming a low-boiling azeotrope with water. The invention also relates to a method of producing a compound of formula 2, a method of producing a compound of formula from a compound of formula 1 and a compound of formula 2.

EFFECT: method enables to obtain a product with high output.

20 cl, 15 tbl, 8 ex

FIELD: chemistry.

SUBSTANCE: invention relates to the chemistry of diphenyl oxide derivatives and specifically to novel 3-phenoxyphenyl-containing 1,3-diketones, intermediate compounds in synthesis of a wide range of biologically active substances of general formula , for example as starting compounds for producing chelate complexes thereof with copper (II) ions of general formula , which have potential for use as extraction agents, analytical reagents of rare-earth elements, vital semiproducts in synthesis of probable biologically active substances. The invention also relates to a method of producing 3-phenoxyphenyl-containing 1,3-diketones, involving reaction of 3-phenoxybenzonitrile with lower alcohols: methanol, ethanol in molar ratio 1:4.245, respectively, in the presence of concentrated sulphuric acid for 7-8 hours, to form alkyl-3-phenoxybenzoate, and subsequent reaction thereof with ketones selected from: acetone, 2-butanone, acetophenone in molar ratio 2.0:1, respectively, in a medium of pure cyclohexane at boiling point thereof in the presence of catalytic amounts of sodium hydride for 2.5-3 hours, followed by extraction of the end product.

EFFECT: wider range of diphenyl oxide derivatives and obtaining 3-phenoxyphenyl-containing 1,3-diketones and chelate complexes thereof with copper (II) ions with high output.

2 cl, 6 ex

FIELD: chemistry.

SUBSTANCE: invention refers to production method of 1-(4-chlorophenyl)-2-cyclopropylpropane-1-one being a by-product for making biologically active substances, as well as to production method for 1-(4-chlorophenyl)-2-methyl-3-butene-1-one being a by-product for making 1-(4-chlorophenyl)-2-cyclopropylpropane-1-one. Production method for 1-(4-chlorophenyl)-2-cyclopropylpropane-1-one consists that 4-chlorobenzonitrile reacts with crotyl chloride or bromide and zinc in organic solvent and optionally with aluminium chloride. Hydrolysis of reaction mixture 2M with hydrochloric acid results in separation 1-(4-chlorophenyl)-2-methyl-3-butene-1-one thereafter purified. It reacts dibromomethane, zinc and copper monochloride in organic solvent with catalyst added or in ultrasonic bath. It is followed with separation of end product by common method.

EFFECT: simple and cheaper end production methods.

4 cl, 2 dwg, 9 ex

The invention relates to the chemistry of adamantane derivatives, and in particular to a new method of obtaining-adamantylidene aldehydes of General formula

where R1=H, R2=CH3WITH3H7WITH4H9; R1=R2=CH3,which are intermediates for the synthesis of biologically active substances, using the adamantane derivative

The invention relates to a method for 5,5'-(oxydi)pentanone-2, which can be used as polyfunctional solvent, extractant, as a fragrant substance and as a feedstock for the synthesis of heterocycles

The invention relates to a method for producing 5-alkoxyethanol-2 formula CH3WITH(CH2)3OR, where R = CnH2n+1n = 1-10, the interaction of acetylchloride (ADC) with a monohydroxy alcohol R-OH in the presence of palladium catalyst in water in the presence of the source of the alcohol R-OH as solvent or water-air environment at a temperature of 165-200C for 6-60 hours at a molar ratio of the components: [ADC]:[R-HE]:[H2O]:[cat]:[solvent] = 1:1: (3-8) : (0,005-0,01) : (2-9), where R = CnH2n+1(n = 1-3) solvent - the corresponding alcohol, and when n4 solvent: diethyl ether

FIELD: chemistry.

SUBSTANCE: invention refers to production method of 1-(4-chlorophenyl)-2-cyclopropylpropane-1-one being a by-product for making biologically active substances, as well as to production method for 1-(4-chlorophenyl)-2-methyl-3-butene-1-one being a by-product for making 1-(4-chlorophenyl)-2-cyclopropylpropane-1-one. Production method for 1-(4-chlorophenyl)-2-cyclopropylpropane-1-one consists that 4-chlorobenzonitrile reacts with crotyl chloride or bromide and zinc in organic solvent and optionally with aluminium chloride. Hydrolysis of reaction mixture 2M with hydrochloric acid results in separation 1-(4-chlorophenyl)-2-methyl-3-butene-1-one thereafter purified. It reacts dibromomethane, zinc and copper monochloride in organic solvent with catalyst added or in ultrasonic bath. It is followed with separation of end product by common method.

EFFECT: simple and cheaper end production methods.

4 cl, 2 dwg, 9 ex

FIELD: chemistry.

SUBSTANCE: invention relates to the chemistry of diphenyl oxide derivatives and specifically to novel 3-phenoxyphenyl-containing 1,3-diketones, intermediate compounds in synthesis of a wide range of biologically active substances of general formula , for example as starting compounds for producing chelate complexes thereof with copper (II) ions of general formula , which have potential for use as extraction agents, analytical reagents of rare-earth elements, vital semiproducts in synthesis of probable biologically active substances. The invention also relates to a method of producing 3-phenoxyphenyl-containing 1,3-diketones, involving reaction of 3-phenoxybenzonitrile with lower alcohols: methanol, ethanol in molar ratio 1:4.245, respectively, in the presence of concentrated sulphuric acid for 7-8 hours, to form alkyl-3-phenoxybenzoate, and subsequent reaction thereof with ketones selected from: acetone, 2-butanone, acetophenone in molar ratio 2.0:1, respectively, in a medium of pure cyclohexane at boiling point thereof in the presence of catalytic amounts of sodium hydride for 2.5-3 hours, followed by extraction of the end product.

EFFECT: wider range of diphenyl oxide derivatives and obtaining 3-phenoxyphenyl-containing 1,3-diketones and chelate complexes thereof with copper (II) ions with high output.

2 cl, 6 ex

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing a compound of formula , where Z is optionally substituted phenyl and Q is phenyl or 1-naphthalenyl, each optionally substituted. The method involves distillation of water from a mixture containing a compound of formula , a compound of formula , a base containing at least one compound selected from a group comprising alkali-earth metal hydroxides of formula 4 M(OH)2, where M is Ca, Sr or Ba, alkali metal carbonates of formula 4a (M1)2CO3 , where M1 is Li, Na or K, 1,5-diazabicyclo[4,3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene, and an aprotic solvent capable of forming a low-boiling azeotrope with water. The invention also relates to a method of producing a compound of formula 2, a method of producing a compound of formula from a compound of formula 1 and a compound of formula 2.

EFFECT: method enables to obtain a product with high output.

20 cl, 15 tbl, 8 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to the method of producing 1-adamantyl-acetaldehyde, used as a valuable intermediate product for synthesis of bioactive substances and functional organic materials. The method comprises a catalytic reaction between 1-adamantanol and vinyl acetate as an unsaturated compound. Vinyl acetate, 2.5-fold molar excess relative to 1-adamantanol; the reaction is caried out for 2 hours in dichloroethane at dichloroethane boiling point, indium tribromide is used as a catalyst, 5 mole %.

EFFECT: target product produced using a simple process and readily available raw materials.

2 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a process for the preparation of (13Z)-acose-13-en-10-one, which, in a 20:1 mixture with the minor component (12Z)-nonadec-12-en-9-one, is identified as the sexual pheromone of peach Moth-eaters of Casposina niponensis. The method consists in the fact that the double carbon-carbon bond of the (Z)-configuration is formed as a result of stereoselective Fe(acac)3-catalyzed cross-coupling of ethyl (4Z)-5-chloropent-4-enoate with n-hexyl magnesium bromide in a mixture of tetrahydrofuran and N-methylpyrrolidone to give ethyl (4Z)-undec-4-enoate, then alkaline hydrolysis of ethyl (4Z)Undec-4-enoate to give (4Z)-undec-4-enoic acid, it is transformed into the acid chloride and a second Fe(acac)3-catalyzed cross-combination of the obtained acid chloride with n-nonylmagnesium bromide.

EFFECT: method allows to obtain the target product at the key stage of cross-coupling with a higher yield.

4 ex

FIELD: chemistry.

SUBSTANCE: invention relates to the method for obtaining aromatic acetylene ketones of the common formula

,

where Ar, Ar' - aromatic radicals, which find a wide variety of applications in the synthesis of various heterocyclic compounds. The method comprises reacting an acetylene component with aldehyde in the presence of Lewis acid in an organic solvent. Tin tetraalkynides are used as an acetylene component in toluene at a temperature of 40-60C for 4-6 hours using zinc chloride as a Lewis acid according to the scheme:

.

2 equivalents of aldehyde are spent for 1 equivalent of the acetylene fragment.

EFFECT: method allows to obtain target products using a simple technology.

1 tbl, 10 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to the method of producing 1-adamantyl-acetaldehyde, used as a valuable intermediate product for synthesis of bioactive substances and functional organic materials. The method comprises a catalytic reaction between 1-adamantanol and vinyl acetate as an unsaturated compound. Vinyl acetate, 2.5-fold molar excess relative to 1-adamantanol; the reaction is caried out for 2 hours in dichloroethane at dichloroethane boiling point, indium tribromide is used as a catalyst, 5 mole %.

EFFECT: target product produced using a simple process and readily available raw materials.

2 tbl, 1 ex

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