37 results about "Perkin reaction" patented technology

The invention discloses 3,4-dihydro-4-aryl coumarin derivatives as well as a preparation method and application thereof. The preparation method comprises the following steps of: with substituted benzaldehyde and malonic acid as raw materials, heating in the presence of pyridine and piperidine and generating a Perkin reaction and a decarboxylic reaction to obtain substituted phenylacrylic acid derivatives; and then subjecting the substituted phenylacrylic acid derivatives and phenol compounds to a reaction in the presence of the catalysis of boron trifluoride diethyl ether and phosphorus oxychloride to obtain the 3,4-dihydro-4-aryl coumarin compounds. The compounds can be used for preparing medicaments for resisting tumors, abnormal vascular proliferation, bacterial and oxidation.

The invention discloses the synthesis of pterostilbene. The method comprises the following steps: using p-hydroxyphenyl acetic acid and veratraldehyde as raw material, carryingout Perkin reaction, getting (Z)-2(4-acetoxylation phenyl)-3-(3, 5- dimethoxy benzoic) acroleic acid, deacetylation, decarboxylation, and getting pterostilbene. The invention has the advantages of cheap raw material, simple technology, easy operation and high productivity. The invention has the advantages of low cost, good economy benefit and environment protection.

The invention discloses a synthetic method of 2-(4-hydroxyphenyl)-5,7-dimethoxy benzofuran. The synthetic method comprises the following steps of: firstly, performing bromination reaction and Perkin reaction on 3,5-dimethoxy phenylacetic acid and parahydroxyben-zaldehyde which are used as raw materials to obtain 2-(2-bromo-3,5-dimethoxy phenyl)-3-(4-hydroxyphenyl) acroleic acid; then performing series-wound hydroxylation/intramolecular cyclization/dehydrogenation reaction to obtain 2-(4-hydroxyphenyl)-5,7-dimethoxy benzofuran-3-carboxylic acid; and finally, performing decarboxylic reaction to prepare the 2-(4-hydroxyphenyl)-5,7-dimethoxy benzofuran. According to the method, raw materials are low in price and easy to obtain, the synthetic route is simple, quick and efficient, a noble metal and a ligand are not needed for catalysis, and the method is simple and convenient to operate and good in atom economy.

The invention is a method for catalytic synthesis of cinnamic acid by water-soluble calixarene phenolate, belonging to the technical field of preparation of organic compounds. The method comprises thefollowing steps: with the water-soluble calixarene phenolate as a catalyst, allowing the water-soluble calixarene phenolate to catalyze benzaldehyde and acetic anhydride to generate a perkin reaction, or catalyze benzaldehyde and propane diacid to generate a Knoevenagel reaction so as to prepare the cinnamic acid, wherein the calixarene phenolate can be repeatedly utilized for a plurality of times. According to the invention, the calixarene phenolate is calixarene phenolate sodium(possitium) salt which is formed through a reaction of calix[n]arene sulfonic acid (n is equal to 4, 6 and 8) andthiocalix[4]arene sulfonic acid with NaOH, KOH, Na2CO3 and K2CO3; and the usage amount of the calixarene phenolate accounts for 5 to 10% of the mass of the benzaldehyde. In the perkin reaction, the mass ratio of the benzaldehyde to the acetic anhydride is 1: 1 to 1: 4; the temperature of the reaction is 140 to 170 DEG C; and the time of the reaction is 1 to 2 h. In the Knoevenagel reaction, the mass ratio of the benzaldehyde to the propane diacid is 1: 1 to 1: 4; the temperature of the reaction is 120 to 150 DEG C; and the time of the reaction is 1 to 2 h. The process of the reaction does notgenerate three industrial wastes like waste gas, waste water and waste residue and is a green chemical process, so the pollution to the environment is reduced; and after completion of the reaction, the product is easily to be separated from the catalyst. The method provided by the invention has the advantages of simple process, high yield, environmental friendliness and low cost, and is a method applicable to industrial production.

The invention discloses a synthesis method and application of intermediates of a sulindac analogue, relating to intermediates of a sulindac analogue. The intermediates are 5-fluoro-2-metyl-3-indene ethyl acetate (5a) and 5-fluoro-2-metyl-3-indene acetic acid (5b). The synthesis method comprises the following steps of: subjecting 4-fluorobenzaldehyde as an initial raw material, propionic anhydride as a solvent and propionic anhydride to a perkin reaction to obtain 4-fluoro-2-metyl-methylcinnamic acid; catalyzing the 4-fluoro-2-metyl-methylcinnamic acid with palladium carbon with the palladium content of 5-20 percent and reducing in the hydrogen gas atmosphere to obtain 3-(4-fluorine phenyl)-2-methyl propionate; subjecting the 3-(4-fluorine phenyl)-2-methyl propionate to the intramolecilar friedel-crafts acyl browning reaction under the action of polyphosphoric acid under the heating condition to form 6-fluoro-2-methyl indene ketone; and subjecting the 6-fluoro-2-methyl indene ketone and halogenated acetate to reformatsky reaction under the action of the activated zinc powder to obtain a crude product and eliminating the crude product in an acid solution to obtain 5-fluoro-2-metyl-3-indene acetate. The intermediates can be used for preparing novel sulindac analogues with anticancer activity.

The invention belongs to the synthesis field of isotope labeled compound synthesis, and particularly relates to scopoletin labeled by stable isotope and a synthetic method for the scopoletin. The synthetic method is characterized in that scopoletin labeled acetylchloride-2-13 C is taken as a raw material, and the scopoletin labeled acetylchloride-2-13C reacts with 2,4-dihydroxyl-5-methoxybenzaldehyde to generate 2-aldehyde-4-methoxy-5-hydroxyl phenyl acetate; under the action of a basic catalyst, scopoletin-2-13C is generated through Perkin reaction. The synthetic method is simple in synthesis step, is gentle in reaction condition, is simple and convenient in operation, is high in product yield being 26% or higher, is capable of effectively synthesizing an isotope labeled coumarin derivative, so that a novel way is provided for synthesizing the isotope labeled coumarin derivative. Certain innovation and unique research significance are achieved on organic synthetic method.

The invention discloses a method for preparing trans polyhydroxystilbene compounds. The method comprises the following steps: 3,5-dibromophenylacetic acid is converted into 3,5-dihydroxyphenyl acetic acid under alkali conditions;3,5-dihydroxyphenyl acetic acid and 4-hydroxybenzaldehyde compounds are subject to a Perkin reaction to obtain E-2-(3,5-diacetyl phenyl)-3-(4'-acetoxyl phenyl)acrylic acid compounds; and the E-2-(3,5-diacetyl phenyl)-3-(4'- acetoxyl phenyl)acrylic acid compounds are subject to decarboxylation isomerization and hydrolysis reaction, or hydrolysis and decarboxylation isomerization reaction to obtain the trans polyhydroxystilbene compounds. The all-trans products obtained by using the method have the advantages of favorable atom economy, simple synthetic route, simpleaftertreatment, low cost, high yield and the like, and can easily realize large-scale preparation.

The invention aims to provide a preparation method of Sarpogrelate intermediate 2-((3-methoxy) phenethyl) phenol (I), which comprises the following steps of: 1) carrying out perkin reaction on 3-methoxyphenylacetic acid (II), salicylic aldehyde (III), organic base and acetic anhydride; 2) further obtaining 2-(3-methoxyphenyl)-3-(2-acetoxy-phenyl) acrylic acid (IV); 3) decarboxylating a compound IV under the existence of quinoline and metal copper to obtain 3-methoxy-2'-acetoxy stilbene (V); 4) hydrolyzing the compound IV to obtain 2-((3-methoxy) styryl) phenol (VI); and 5) carrying out catalytic hydrogenation on the compound IV to obtain a compound I. The technical scheme disclosed by the invention has the characteristics of simplicity in operation, mild reaction condition, no hydroxyl protection or deprotection required, easiness for product purification, short synthetic route, easiness for material obtaining, high yield, low cost and the like and has a wide industrial application prospect.

The invention discloses a method for preparing a caffeic acid derivative. A compound shown as the formula II serves as a raw material to be subjected to a substitution reaction with haloalkane to prepare a compound shown as the formula III, and the compound shown as the formula III and acetic anhydride are subjected to a Perkin reaction to prepare a compound shown as the formula I, namely, the target object caffeic acid derivative, wherein the structures of the compounds shown as the formula I, the formula II and the formula III are shown in the specification, wherein R represents methyl or cyclopropyl cyclopropyl. According to the method, the synthetic route is short, the product yield is high, adopted reagents are low in toxicity and safe, the production cost is low, and the method is suitable for large-scale industrial production.

The invention discloses a preparation method and application of Z-3,4,4',5-tetramethoxy-2',3'-dihydroxy diphenylethylene. The preparation method comprises the following steps of: taking 2,3,4-trihydroxy phenylfluorone as a raw material; carrying out single methylation on the 2,3,4-trihydroxy phenylfluorone; carrying out substitution reaction on the methylated 2,3,4-trihydroxy phenylfluorone with bromopropane so as to obtain 2,3-diisopropoxy-4-methoxybenzaldehyde; carrying out Perkin reaction on 2,3-diisopropoxy-4-methoxybenzaldehyde with 3,4,5-trimethoxyphenylacetic acid so as to obtain E-2-(3,4,5-trimethoxyphenyl)-3-(2',3'-diisopropoxy-4'-methoxyphenyl)acrylic acid; carrying out decarboxylation to obtain Z-3,4,4',5-tetramethoxy-2',3'-diisopropoxy diphenylethylene; and finally obtaining Z-3,4,4',5-tetramethoxy-2',3'-dihydroxy diphenylethylene after carrying out deprotection. The synthetic route provided by the invention is simple and direct, cis-selectivity is higher, and the yield of the Perkin reaction as well as the total yield of Z-3,4,4',5-tetramethoxy-2',3'-dihydroxy diphenylethylene are both higher. The preparation method disclosed by the invention has the characteristics of simpleness and feasibility for operation, low price and easy obtainment of used raw materials and reagents, small pollution on environment, good atom economy, low cost and capability of being applied to industrialized production.

The invention discloses a new synthetic method of 4-halogenated phenylacetylene, which comprises the following steps: taking 4-halogenated benzaldehyde and acetic anhydride which are cheap and are easy to obtain as raw materials and obtaining the 4-halogenated benzaldehyde which is a final target product through Perkin reaction, bromination reaction and debromination, decarboxylation and elimination reaction. The new synthetic method has the benefits that as the 4-halogenated benzaldehyde and the acetic anhydride are taken as substrates, and an environmental protection solvent with low toxicity is adopted in the reaction process, the new synthetic method has the characteristics of greenness and environmental protection, high efficiency, low cost, reasonable yield, mild reaction conditions and easiness in control; through the optimization of the reaction conditions and a post-processing method, in particular to an innovative application of a sublimation method to product purification, the new synthetic method disclosed by the invention also has the characteristic of high product purity.

The invention provides a refining method of a coumarin crude product. The refining method comprises the following steps of first mixing the coumarin crude product prepared through a perkin reaction and water, so as to obtain a water-containing coumarin crude product; afterwards, subjecting the water-containing coumarin crude product to a coarse water removal process, a phenyl ester removal process, before-removal rectification process and a finished product outputting process in sequence through continuous rectification, so as to obtain a coumarin pure product. According to the refining method, through controlling process conditions in the coarse water removal process, the phenyl ester removal process, the before-removal rectification process and the finished product outputting process, a purification method provided by the invention can be used for realizing the continuous rectification; not only are the quality and the yield of a coumarin rectified product guaranteed, but also the high efficiency and the energy conservation of the rectification are guaranteed.

The invention relates to the field of medicine synthesis, in particular to a preparation method of gliclazide and an intermediate of gliclazide. The preparation method comprises a Mannich reaction, an amino protection reaction, a Perkin reaction, an epoxidation reaction, a hydrolysis reaction, a decarboxylation reaction and a reductive amination reaction. The preparation method is mild in reaction condition, green and environment-friendly, few three wastes are generated, a high-risk reducing agent does not need to be used, nitrosation reaction does not need to be carried out, and introduction of nitroso-nitroso impurities is successfully avoided.