CN107522626A - A kind of method based on WK reactions and VHA reaction synthesizing aldehyde compounds - Google Patents
A kind of method based on WK reactions and VHA reaction synthesizing aldehyde compounds Download PDFInfo
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- CN107522626A CN107522626A CN201710832996.6A CN201710832996A CN107522626A CN 107522626 A CN107522626 A CN 107522626A CN 201710832996 A CN201710832996 A CN 201710832996A CN 107522626 A CN107522626 A CN 107522626A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/02—Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
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Abstract
Synthesis of carboxylic acid class compound is reacted by Willgerodt Kindler the invention discloses a kind of method based on Willgerodt Kindler reactions and Vilsmeier Haack Arnold reaction synthesizing aldehyde compounds, including using acyl compounds as raw material；Prepare Vilsmeier Haack Arnold reagents；Carboxylic acid compound is added salt condensing agent is synthesized in Vilsmeier Haack Arnold reagents；Salt condensing agent is hydrolyzed to obtain aldehyde compound.Synthetic route of the present invention is reasonable, method is reliable and stable, combined coefficient is high, carboxylic acid compound, salt condensing agent and aldehyde compound can be obtained simultaneously, have broad application prospects and huge commercial value, enrich inorganic and organic compound species, and inorganic and organic field synthetic method.
Description
Technical field
The present invention relates to synthesizing aldehyde compound, more particularly to it is a kind of based on Willgerodt-Kindler (WK) reactions and
The method that Vilsmeier-Haack-Arnold (VHA) reacts synthesizing aldehyde compound.
Background technology
Metal Porous-Organic material (MOF) and covalent organic porous material (COF) are twentieth century end and 21st century
The new porous material of two classes just risen, gas absorption with separating, chemical co-ordination, heterocatalysis, drug delivery, electronics
The multiple fields such as device suffer from good application.In the design building-up process of MOF materials and COF materials, it is indispensable just
It is organic ligand.Organic ligand can have a variety of designs and selection, rely on the organic synthesis technology of present mature, almost
Any organic ligand that you want can be obtained, to be assembled into different MOF materials and COF materials.There is powerful synthesis
Learn to rely on, porous material also just has Protean ability.
Aldehyde compound is rare excellent part and predecessor in MOF and COF fields, available for synthesizing multiclass
New metal is organic and adds organic porous material altogether, the development in this two big field can be greatly facilitated, accordingly, with respect to aldehydes
The research of compound suffers from for abundant inorganic and organic compound species, and the reference of inorganic and organic field synthetic method
Important meaning.
The content of the invention
In view of this, the embodiment provides a kind of synthetic route is reasonable, method is reliable and stable, and combined coefficient is high
Based on Willgerodt-Kindler reaction and Vilsmeier-Haack-Arnold reaction synthesizing aldehyde compound method.
Embodiments of the invention provide a kind of based on Willgerodt-Kindler reactions and Vilsmeier-Haack-
The method that Arnold reacts synthesizing aldehyde compound, comprises the following steps：
S1. synthesis of carboxylic acid class compound is reacted by Willgerodt-Kindler using acyl compounds as raw material；
S2. Vilsmeier-Haack-Arnold reagents are prepared；
S3. carboxylic acid compound step S1 obtained adds Vilsmeier-Haack-Arnold prepared by step S2 and tried
Salt condensing agent is synthesized in agent；
S4. the salt condensing agent that step S3 is obtained is hydrolyzed to obtain aldehyde compound.
Further, in the step S1, the specific method of synthesis of carboxylic acid class compound is：
S1.1. acyl compounds, sulphur and morpholine are reacted into 24h under nitrogen protection, reaction temperature is 140 DEG C；
S1.2. cool down, add 1.4- dioxane, normal-temperature reaction 30min, obtained reaction solution is poured into the burning for filling water
In cup, filtration washing；
S1.3. the solid being filtrated to get is added in sodium hydrate aqueous solution and reacts 16h, reaction temperature is 100 DEG C；
S1.4. hydrochloric acid is added to acidity, filtration washing；
S1.5. by the solid dissolving being filtrated to get in sodium hydrate aqueous solution；
S1.6. hydrochloric acid precipitation is added, is filtered；
S1.7. step S1.5-S1.6 is repeated 3-5 times, that is, obtains carboxylic acid compound.
Further, in the step S2, the preparation method of Vilsmeier-Haack-Arnold reagents is：In condition of ice bath
Under, appropriate POCl3 is slowly at the uniform velocity instilled in anhydrous dimethyl formamide, drop finishes, and reacts 30min, that is, is made
Vilsmeier-Haack-Arnold reagents.
Further, in the step S3, the specific method of synthesis salt condensing agent is：
S3.1. carboxylic acid compound is added in Vilsmeier-Haack-Arnold reagents, and is passed through nitrogen as guarantor
Gas is protected, reacts 48h, reaction temperature is 100 DEG C；
S3.2. cool down, add trash ice and decompose unnecessary Vilsmeier-Haack-Arnold reagents；
S3.3. the aqueous solution dissolved with sodium perchlorate is added, is stirred, stands or refrigerates, filtering, that is, obtains salt condensation
Agent.
Further, the specific method for aldehyde compound being prepared in the step S4 is：
S4.1. sodium hydroxide is dissolved in appropriate distilled water；
S4.2. salt condensing agent is added, and is passed through nitrogen as protection gas, stirring reaction 12h；
S4.3. cool down, addition hydrochloric acid to pH is 1；
S4.4. q. s. methylene chloride is added, is stirred, is stood, filtering, that is, obtains aldehyde compound.
Further, the acyl compounds are 1,3,5- tri- (4- acetylphenyls) benzene, and the carboxylic acid compound is
1,3,5- tri- (4- acetates phenyl) benzene, the salt condensing agent are triphenylbenzene salt, and the aldehyde compound is 1,3,
5- tri- (4- glyoxals phenyl) benzene.
Further, the acyl compounds are three (4- acetylphenyls) amine, and the carboxylic acid compound is three (4- second
Acidic group phenyl) amine, the salt condensing agent is triphenyl amine salt, and the aldehyde compound is three (4- glyoxals phenyl)
Amine.
Compared with prior art, the invention has the advantages that：Synthetic route is reasonable, and method is reliable and stable, synthesis
Efficiency high, can obtain carboxylic acid compound, salt condensing agent and aldehyde compound simultaneously, and various compounds suffer from good
Yield and purity, greatly improve economic benefit, and carboxylic acid compound and aldehyde compound possess abundant functional group and perfect right
Title property, is widely used and good Modulatory character in the design of structural framing, it is new to can be widely applied to composite structure
The porous material of grain husk, has broad application prospects and huge commercial value, enriches inorganic and organic compound species, with
And inorganic and organic field synthetic method.
Brief description of the drawings
Fig. 1 is of the invention a kind of based on Willgerodt-Kindler reactions and Vilsmeier-Haack-Arnold reactions
One flow chart of the method for synthesizing aldehyde compound.
Fig. 2 is the particular flow sheet of step S1 in Fig. 1.
Fig. 3 is the particular flow sheet of step S3 in Fig. 1.
Fig. 4 is the particular flow sheet of step S4 in Fig. 1.
Embodiment
To make the object, technical solutions and advantages of the present invention clearer, below in conjunction with accompanying drawing to embodiment party of the present invention
Formula is further described.
Refer to Fig. 1, the embodiment provides one kind based on Willgerodt-Kindler reaction and
The method that Vilsmeier-Haack-Arnold reacts synthesizing aldehyde compound, comprises the following steps：
S1. synthesis of carboxylic acid class compound is reacted by Willgerodt-Kindler using acyl compounds as raw material；
Fig. 2 is refer to, specific method is：
S1.1. acyl compounds, sulphur and morpholine are reacted into 24h under nitrogen protection, reaction temperature is 140 DEG C；
S1.2. cool down, add 1.4- dioxane, normal-temperature reaction 30min, obtained reaction solution is poured into the burning for filling water
In cup, filtration washing；
S1.3. the solid being filtrated to get is added in sodium hydrate aqueous solution and reacts 16h, reaction temperature is 100 DEG C；
S1.4. hydrochloric acid is added to acidity, filtration washing；
S1.5. by the solid dissolving being filtrated to get in sodium hydrate aqueous solution；
S1.6. hydrochloric acid precipitation is added, is filtered；
S1.7. step S1.5-S1.6 is repeated 3-5 times, that is, obtains carboxylic acid compound.
S2. Vilsmeier-Haack-Arnold reagents are prepared；
Under condition of ice bath, appropriate POCl3 is slowly at the uniform velocity instilled in anhydrous dimethyl formamide, drop finishes, reaction
30min, that is, Vilsmeier-Haack-Arnold reagents are made.
S3. carboxylic acid compound step S1 obtained adds Vilsmeier-Haack-Arnold prepared by step S2 and tried
Salt condensing agent is synthesized in agent；
Fig. 3 is refer to, specific method is：
S3.1. carboxylic acid compound is added in Vilsmeier-Haack-Arnold reagents, and is passed through nitrogen as guarantor
Gas is protected, reacts 48h, reaction temperature is 100 DEG C；
S3.2. cool down, add trash ice and decompose unnecessary Vilsmeier-Haack-Arnold reagents；
S3.3. the aqueous solution dissolved with sodium perchlorate is added, is stirred, stands or refrigerates, filtering, that is, obtains salt condensation
Agent.
S4. the salt condensing agent that step S3 is obtained is hydrolyzed to obtain aldehyde compound；
Fig. 4 is refer to, specific method is：
S4.1. sodium hydroxide is dissolved in appropriate distilled water；
S4.2. salt condensing agent is added, and is passed through nitrogen as protection gas, stirring reaction 12h；
S4.3. cool down, addition hydrochloric acid to pH is 1；
S4.4. q. s. methylene chloride is added, is stirred, is stood, filtering, that is, obtains aldehyde compound.
In one embodiment, acyl compounds 1,3,5- tri- (4- acetylphenyls) benzene, the carboxylic acid compound
For 1,3,5- tri- (4- acetates phenyl) benzene, the salt condensing agent is triphenylbenzene salt, and the aldehyde compound is 1,
3,5- tri- (4- glyoxals phenyl) benzene.
By 1,3,5- tri- (4- acetates phenyl) benzene, sulphur and morpholine under nitrogen protection, 24h is reacted, reaction temperature is
140 DEG C, cooling, add 1.4- dioxane, normal-temperature reaction 30min；Reaction solution is poured into the beaker for filling a large amount of water, filtered
Washing；The solid of filtering is added in sodium hydrate aqueous solution and reacts 16h, reaction temperature is 100 DEG C；Add hydrochloric acid to acidity, mistake
Filter washing；Dissolve again in sodium hydroxide solution, add hydrochloric acid precipitation, filtering, be repeated several times, obtain 1,3,5- tri- (4- acetic acid
Base phenyl) benzene.
Under condition of ice bath, appropriate POCl3 is slowly at the uniform velocity instilled into anhydrous dimethyl formamide (DMF), drop finishes, instead
30min is answered, Vilsmeier-Haack-Arnold reagents are made.
1,3,5- tri- (4- acetates phenyl) benzene are added into Vilsmeier-Haack-Arnold reagents, leads to nitrogen and protects
Shield, reacts 48h, and reaction temperature is 100 DEG C；Cooling, trash ice is added to decompose unnecessary Vilsmeier-Haack-Arnold reagents；Add
Entering the aqueous solution dissolved with sodium perchlorate, stir, stand or refrigeration, filtering, it is triphenylbenzene salt to obtain brownish-yellow powder, and three
The yield of phenyl benzene salt is 94.3%.
Sodium hydroxide is dissolved in appropriate distilled water, rear to add triphenylbenzene salt, nitrogen protection, stirring reaction 12h is cold
But, it is 1 to add hydrochloric acid to pH, adds q. s. methylene chloride, stirs, stand, filtering, it is 1,3,5- tri- (4- second to obtain brown solid
Dialdehyde-based phenyl) benzene.
In another embodiment, the acyl compounds are three (4- acetylphenyls) amine, the carboxylic acid compound
For three (4- acetates phenyl) amine, the salt condensing agent is triphenyl amine salt, and the aldehyde compound is three (4- second two
Aldehyde radical phenyl) amine.
By three (4- acetylphenyls) amine, sulphur and morpholines under nitrogen protection, 24h is reacted, reaction temperature is 140 DEG C,
Cooling, add 1.4- dioxane, normal-temperature reaction 30min；Reaction solution is poured into the beaker for filling a large amount of water, filtration washing；
The solid of filtering is added in sodium hydrate aqueous solution and reacts 16h, reaction temperature is 100 DEG C；Hydrochloric acid is added to cross diafiltration to acidity
Wash；Dissolve again in sodium hydroxide solution, add hydrochloric acid precipitation, filtering, be repeated several times, obtain three (4- acetates phenyl) amine.
Under condition of ice bath, appropriate POCl3 is slowly at the uniform velocity instilled into anhydrous dimethyl formamide (DMF), drop finishes, instead
30min is answered, Vilsmeier-Haack-Arnold reagents are made.
Three (4- acetates phenyl) amine are added into Vilsmeier-Haack-Arnold reagents, lead to nitrogen protection, reaction
48h, reaction temperature are 100 DEG C；Cooling, trash ice is added to decompose unnecessary Vilsmeier-Haack-Arnold reagents；Add dissolved with
The aqueous solution of sodium perchlorate, stirring are stood or refrigeration, and filtering, it is triphenyl amine salt to obtain dark brown powder, triphenylamine
The yield of salt is 96%.
Sodium hydroxide is dissolved in appropriate distilled water, rear to add triphenyl amine salt, nitrogen protection, stirring reaction 12h is cold
But, it is 1 to add hydrochloric acid to pH, adds q. s. methylene chloride, stirs, stand, filtering, it is three (4- glyoxals to obtain brown solid
Phenyl) amine.
Synthetic route of the present invention is reasonable, and method is reliable and stable, and combined coefficient is high, can obtain simultaneously carboxylic acid compound,
Salt condensing agent and aldehyde compound, various compounds suffer from good yield and purity, greatly improve economic benefit, carboxylic acid
Class compound and aldehyde compound possess abundant functional group and perfect symmetry, widely should have in the design of structural framing
With with good Modulatory character, can be widely applied to the novel porous material of composite structure, have broad application prospects and
Huge commercial value, enrich inorganic and organic compound species, and inorganic and organic field synthetic method.
In the case where not conflicting, the feature in embodiment and embodiment herein-above set forth can be combined with each other.
Above-mentioned case study on implementation is only to illustrate the application example to be clear, and is not the restriction to embodiment,
Herein there is no need to be exhaustive to all implementations.On the basis of the above description, extended out aobvious and
Among the change or variation being clear to are still in the protection domain of this patent.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all the present invention spirit and
Within principle, any modification, equivalent substitution and improvements made etc., it should be included in the scope of the protection.
Claims (7)
1. one kind is based on Willgerodt-Kindler reactions and Vilsmeier-Haack-Arnold reaction synthesizing aldehyde chemical combination
The method of thing, it is characterised in that comprise the following steps：
S1. synthesis of carboxylic acid class compound is reacted by Willgerodt-Kindler using acyl compounds as raw material；
S2. Vilsmeier-Haack-Arnold reagents are prepared；
S3. carboxylic acid compound step S1 obtained is added in Vilsmeier-Haack-Arnold reagents prepared by step S2
Synthesize salt condensing agent；
S4. the salt condensing agent that step S3 is obtained is hydrolyzed to obtain aldehyde compound.
It is 2. according to claim 1 anti-based on Willgerodt-Kindler reactions and Vilsmeier-Haack-Arnold
The method for answering synthesizing aldehyde compound, it is characterised in that in the step S1, the specific method of synthesis of carboxylic acid class compound is：
S1.1. acyl compounds, sulphur and morpholine are reacted into 24h under nitrogen protection, reaction temperature is 140 DEG C；
S1.2. cool down, add 1.4- dioxane, normal-temperature reaction 30min, obtained reaction solution is poured into the beaker for filling water
In, filtration washing；
S1.3. the solid being filtrated to get is added in sodium hydrate aqueous solution and reacts 16h, reaction temperature is 100 DEG C；
S1.4. hydrochloric acid is added to acidity, filtration washing；
S1.5. by the solid dissolving being filtrated to get in sodium hydrate aqueous solution；
S1.6. hydrochloric acid precipitation is added, is filtered；
S1.7. step S1.5-S1.6 is repeated 3-5 times, that is, obtains carboxylic acid compound.
It is 3. according to claim 1 anti-based on Willgerodt-Kindler reactions and Vilsmeier-Haack-Arnold
The method for answering synthesizing aldehyde compound, it is characterised in that in the step S2, the system of Vilsmeier-Haack-Arnold reagents
Preparation Method is：Under condition of ice bath, appropriate POCl3 is slowly at the uniform velocity instilled in anhydrous dimethyl formamide, drop finishes, reaction
30min, that is, Vilsmeier-Haack-Arnold reagents are made.
It is 4. according to claim 1 anti-based on Willgerodt-Kindler reactions and Vilsmeier-Haack-Arnold
The method for answering synthesizing aldehyde compound, it is characterised in that in the step S3, the specific method of synthesis salt condensing agent is：
S3.1. carboxylic acid compound is added in Vilsmeier-Haack-Arnold reagents, and is passed through nitrogen and is used as protection gas,
48h is reacted, reaction temperature is 100 DEG C；
S3.2. cool down, add trash ice and decompose unnecessary Vilsmeier-Haack-Arnold reagents；
S3.3. the aqueous solution dissolved with sodium perchlorate is added, is stirred, stands or refrigerates, filtering, that is, obtain salt condensing agent.
It is 5. according to claim 1 anti-based on Willgerodt-Kindler reactions and Vilsmeier-Haack-Arnold
The method for answering synthesizing aldehyde compound, it is characterised in that the specific method that aldehyde compound is prepared in the step S4 is：
S4.1. sodium hydroxide is dissolved in appropriate distilled water；
S4.2. salt condensing agent is added, and is passed through nitrogen as protection gas, stirring reaction 12h；
S4.3. cool down, addition hydrochloric acid to pH is 1；
S4.4. q. s. methylene chloride is added, is stirred, is stood, filtering, that is, obtains aldehyde compound.
It is 6. according to claim 1 anti-based on Willgerodt-Kindler reactions and Vilsmeier-Haack-Arnold
The method for answering synthesizing aldehyde compound, it is characterised in that the acyl compounds are 1,3,5- tri- (4- acetylphenyls) benzene,
The carboxylic acid compound is 1,3,5- tri- (4- acetates phenyl) benzene, and the salt condensing agent is triphenylbenzene salt, institute
It is 1,3,5- tri- (4- glyoxals phenyl) benzene to state aldehyde compound.
It is 7. according to claim 1 anti-based on Willgerodt-Kindler reactions and Vilsmeier-Haack-Arnold
The method for answering synthesizing aldehyde compound, it is characterised in that the acyl compounds are three (4- acetylphenyls) amine, the carboxylic
Acid compounds are three (4- acetates phenyl) amine, and the salt condensing agent is triphenyl amine salt, the aldehyde compound
For three (4- glyoxals phenyl) amine.
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| US6184322B1 (en) * | 1996-06-21 | 2001-02-06 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Metal-containing side chain liquid crystal polymers |
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| CN102816051A (en) * | 2011-06-10 | 2012-12-12 | 苏州卫生职业技术学院 | Process for synthesizing 4-chlorophenyl ethanol |
| CN104086392A (en) * | 2014-07-24 | 2014-10-08 | 宜春学院 | Catalytic synthesis method for biphenylacetic acid |
-
2017
- 2017-09-15 CN CN201710832996.6A patent/CN107522626A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6184322B1 (en) * | 1996-06-21 | 2001-02-06 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Metal-containing side chain liquid crystal polymers |
| CN101928207A (en) * | 2009-06-23 | 2010-12-29 | 兰州大学 | New method for synthesizing aldehyde compound by alkylation reaction |
| CN102816051A (en) * | 2011-06-10 | 2012-12-12 | 苏州卫生职业技术学院 | Process for synthesizing 4-chlorophenyl ethanol |
| CN104086392A (en) * | 2014-07-24 | 2014-10-08 | 宜春学院 | Catalytic synthesis method for biphenylacetic acid |
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| Title |
|---|
| LI SHENGHUI ET AL: "Synthesis and biological evaluation of some novel N-arylpyrazole derivatives as cytotoxic agents", 《RES CHEM INTERMED》 * |
| VASILE LOZAN ET AL: "Tetranuclear Nickel Complexes Composed of Pairs of Dinuclear LNi2 Fragments Linked by 4,4-Bipyrazolyl, 1,4-Bis(4’-pyrazolyl)benzene, and 4,4-Bipyridazine：Synthesis, Structures, and Magnetic Properties", 《EUR.J.INORG.CHEM.》 * |
| 张舟: "对甲氧基苯乙酸高选择性合成反应研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
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Application publication date: 20171229 |