CN108484405A - A kind of carboxylic acid aryl esters compounds process for production thereof based on alkenyl carboxylate's ester exchange reaction - Google Patents
A kind of carboxylic acid aryl esters compounds process for production thereof based on alkenyl carboxylate's ester exchange reaction Download PDFInfo
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- CN108484405A CN108484405A CN201810370711.6A CN201810370711A CN108484405A CN 108484405 A CN108484405 A CN 108484405A CN 201810370711 A CN201810370711 A CN 201810370711A CN 108484405 A CN108484405 A CN 108484405A
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- carboxylic acid
- alkenyl carboxylate
- aryl esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
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Abstract
A kind of carboxylic acid aryl esters compounds process for production thereof based on alkenyl carboxylate's ester exchange reaction, belongs to pharmaceutical-chemical intermediate and related chemistry technical field.This method uses phenol and alkenyl carboxylate as raw material, under base catalysis, realizes the green of carboxylic acid aryl esters compound, efficiently synthesizes.This method have high selectivity, reaction condition is mild, functional group compatibility is good, substrate spectrum is wide, advantages of environment protection.It since carboxylic acid aryl esters compound is a kind of important organic synthesis intermediate, has a very wide range of applications in organic synthesis and pharmaceutical field, therefore, the present invention has larger application value and economic results in society.
Description
Technical field
The present invention relates to pharmaceutical-chemical intermediate and related chemistry technical fields, are related to one kind based on phenol and carboxylic acid alkenyl
The ester exchange reaction of ester, using phenolic compound and alkenyl carboxylate's class compound as the system of the carboxylic acid aryl esters compound of raw material
Preparation Method.
Background technology
Carboxylic acid aryl esters compound is a kind of important synthesis of natural product, drug or functional molecular intermediate, is being had
Machine synthesis field has a very wide range of applications.Carboxylic acid aryl esters compound, the table especially in terms of the synthesis such as medicine and pesticide
Reveal huge purposes, thus the synthesis of carboxylic acid aryl esters compound is current one of research hotspot.Utilize phenol and carboxylic acid halides
Or the acylation of acid anhydrides is a kind of important synthesizing mean of synthesizing aryl ester carboxylic acid, the classical preparation method of aryl ester carboxylic acid be with
Carboxylic acid halides or acid anhydrides are acylting agent, realize the acylation reaction of phenol but such method has the following disadvantages：Carboxylic acid halides or acid anhydrides
High reaction activity cause its selectivity it is low；Functional group compatibility is poor；Post-reaction treatment is difficult；Severe reaction conditions etc..At present
Also develop several other synthesizing aryl ester carboxylic acids reaction system [referring to:(a)Ishii,Y.；Takeno,M.；
Kawasaki,Y.；Muromachi,A.；Nishiyama,Y.；Sakaguchi,S.J.Org.Chem.1996,61,3088-
3092.(b)Tashiro,D.；Kawasaki,Y.；Sakaguchi,S.；Ishii,Y.J.Org.Chem.1997,62,8141-
8144.(c)Grasa,G.A.；Kissling,R.M.；Nolan,S.P.Org.Lett.2002,4,3583-3586.(d)
Sarkar,S.D.；Grimme,S.；Studer,A.J.Am.Chem.Soc.2010,132,1190-1191.(e)Lee,S.Y.；
Murphy,J.M.；Ukai,A.；Fu,G.C.J.Am.Chem.Soc.2012,134,15149-15153.(f)Liu,H.-X.；
Dang,Y.-Q.；Yuan,Y.-F.；Xu,Z.-F.；Qiu,S.-X.；Tan,H.-B.Org.Lett.2016,18,5584–
5587.], but there are severe reaction conditions, precious metal catalyst use, raw material mix is special the shortcomings of.Thus develop
A kind of selectivity and high income, reaction condition are mild, Atom economy is high, the carboxylic acid aryl esters compound of excellent catalytic effect
Synthetic method is of great significance.
Invention content
The present invention provides a kind of ester exchange reaction systems of new alkenyl carboxylate, are used to prepare carboxylic acid aryl esters
Object is closed, this method is raw material using phenol and alkenyl carboxylate's class compound, realizes organic base and the phenol and carboxylic of inorganic base catalysis
The ester exchange reaction of sour alkenyl ester type compound, synthesizing aryl ester carboxylic acid class compound.This method is simple with catalyst system and catalyzing, selects
The advantages that selecting property is good, good, environmental-friendly, the easy realization industrialization of mild condition, Atom economy.The present invention has larger application
Value and economic results in society.
The technical solution adopted by the present invention is：A kind of carboxylic acid aryl esters chemical combination based on alkenyl carboxylate's ester exchange reaction
Object preparation method is reacted using phenol and alkenyl carboxylate's class compound as raw material by base-catalyzed transesterification, and a series of carboxylic acids are synthesized
Aryl ester type compound, this approach includes the following steps：
Synthetic route is as follows：
Wherein：R1=hydrogen, C1-6Linear or branched alkyl group, hydroxyl, amino, halogen, nitro or cyano, R2=hydrogen, C1-6Straight chain
Or branched alkyl, aryl, R3=hydrogen, C1-6Linear or branched alkyl group, R4=C1-5Linear or branched alkyl group, phenyl, p-methylphenyl；
(1) phenol, base catalyst, alkenyl carboxylate's class compound and organic solvent are added sequentially in reactor, 25~
130 DEG C are reacted 8~36h hours；The molar ratio of the phenol and alkenyl carboxylate's class compound is 1:1~1:5, phenol and base catalyst
Molar ratio be 1:0.01~1:0.5；
(2) after reaction, solvent is removed under reduced pressure, carries out silica gel post separation with eluant, eluent, obtains carboxylic acid aryl esters
Close object.
Further,
Wherein：R5For methyl, ethyl or propyl；
(1) naphthols, base catalyst, alkenyl carboxylate's class compound and organic solvent are added sequentially in reactor, 25
~130 DEG C are reacted 8~36h hours；The molar ratio of the phenol and alkenyl carboxylate's class compound is 1:1~1:5, phenol and base catalysis
The molar ratio of agent is 1:0.01~1:0.5；
(2) after reaction, solvent is removed under reduced pressure, carries out silica gel post separation with eluant, eluent, obtains carboxylic acid aryl esters
Close object.
When naphthols and C1-3Vinyl acetate using above-mentioned means synthesize when, yield be more than or equal to 99%.
Phenolic compound include containing alkyl, containing hydroxyl, containing amino, containing halogen, containing nitro, containing cyano,
Phenol containing aryl and naphthols；Alkenyl carboxylate's class compound includes the vinyl acetate containing alkyl or the second containing aromatic ring
Vinyl acetate class compound；R in phenol on aromatic ring1It is hydrogen, C1-6Linear or branched alkyl group, hydroxyl, amino, halogen, nitro or cyanogen
Base；R in alkenyl carboxylate's class compound2It is hydrogen, C1-6Linear or branched alkyl group, aryl；In alkenyl carboxylate's class compound
R3It is hydrogen, C1-6Linear or branched alkyl group；R in alkenyl carboxylate's class compound4It is C1-5Linear or branched alkyl group, phenyl, to first
Phenyl；The molar ratio of indoles and alkenyl carboxylate's class compound is 1:1~1:5.
Range of reaction temperature is 25~130 DEG C, preferably 90~120 DEG C.
Reaction time range is 8~36h, preferably 18~for 24 hours.
Alkali used is organic amine or basic salt, selected from potassium carbonate, calcium carbonate, sodium carbonate, cesium carbonate, sodium bicarbonate, phosphorus
Sour potassium, potassium dihydrogen phosphate, dipotassium hydrogen phosphate, sodium phosphate, potassium hydroxide, sodium hydroxide, calcium hydroxide, ammonium hydroxide, triethylamine, three fourths
Amine, N, N- diisopropyl ethyl amines, pyridine；
The amount of organic solvent is 1~200mL, and it is sub- that the organic solvent is selected from benzene, toluene, Isosorbide-5-Nitrae-dioxane, dimethyl
Sulfone, ethyl alcohol, methanol, the tert-butyl alcohol, isopropanol, dichloromethane, chloroform, n-butyl ether, carbon tetrachloride, dimethyl adipate, second
Acetoacetic ester, petroleum ether, methyl tertiary butyl ether(MTBE), tetrahydrofuran, acetone, N,N-dimethylformamide, acetonitrile, hexamethylene, n-hexane
One or more of.
The molar ratio of phenol and alkali salt catalyst is 1:0.01~1:0.5.
The molar ratio of phenol and alkenyl carboxylate's class compound is 1:1~1:5.
Advantageous effect：The aryl ester carboxylic acid synthetic method of the present invention, has that high selectivity, reaction condition be mild, functional group
Good compatibility, wide application range of substrates, advantages of environment protection, specially：
(1) the use of organic base or inorganic base is catalyst in this method, reduces the cost of catalyst system and catalyzing；Post-reaction treatment
Simply；The problems such as avoiding catalyst poisoning, severe reaction conditions caused by using metallic catalyst.
(2) this method is the ester exchange reaction carried out for substrate phenolic compound, in the prior art because of carboxylic acid halides or acid anhydrides
For the use of acylting agent, reactive functionality poor compatibility, reaction system complexity, severe reaction conditions are caused.In the application,
Because of the use of alkenyl carboxylate's class acylting agent, the tautomerism of product ethylene alcohol is realized in the reaction system, avoids ester
The progress of back reaction is exchanged, mild, simple condition can be used, realize the ester exchange reaction of phenolic compound.
(3) excellent catalytic effect, selectivity and high income, according to the data grasped, in the acylation for the phenol reported at present
In reaction, the relevant report of phenol and the ester exchange reaction of alkenyl carboxylate's class compound is had no.With diisopropyl ethyl amine, pyrrole
As for catalyst, the yield in the application is for pyridine, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium formate, sodium acetate etc.
57% or more, as shown in the table.
To sum up, this method is that selectivity is good, reaction condition is mild, Atom economy is high, the carboxylic of excellent catalytic effect, high income
The synthetic method of sour aryl ester type compound.Since aryl ester carboxylic acid is a kind of important organic synthesis intermediate, led in pharmacy
Domain has a very wide range of applications, and therefore, the present invention has larger application value and economic results in society.
Description of the drawings
Fig. 1 is compound 3a's1H-NMR。
Fig. 2 is compound 3a's13C-NMR。
Fig. 3 is compound 3b's1H-NMR。
Fig. 4 is compound 3b's13C-NMR。
Fig. 5 is compound 3c's1H-NMR。
Fig. 6 is compound 3c's13C-NMR。
Fig. 7 is compound 3d's1H-NMR。
Fig. 8 is compound 3d's13C-NMR。
Fig. 9 is compound 3e's1H-NMR。
Figure 10 is compound 3e's13C-NMR。
Figure 11 is compound 3f's1H-NMR。
Figure 12 is compound 3f's13C-NMR。
Specific implementation mode
The preparation method of aryl ester carboxylic acid of the present invention has raw material cheap and easy to get, good reaction selectivity, reaction item
The advantages that part is mild, environmental-friendly, Atom economy is high shows good application prospect.
Present invention will be further explained below with reference to specific examples.These embodiments are merely to illustrate the present invention and do not have to
In limiting the scope of the invention.Technical staff in the art belongs to this hair to the simple replacement of the invention done or improvement
Within bright protected technical solution.
Embodiment 1：The synthesis of naphthalen-2-yl acetate (3a)
Accurately weigh beta naphthal (72.0mg, 0.5mmol), vinyl acetate (86.1mg, 1.0mmol), triethylamine
(20.4mg, 0.2mmol), and be added sequentially in the Schlenk bottles of 50mL, toluene (5.0mL) is added, is placed in 60 DEG C of oil baths
Reaction is for 24 hours.After reaction, solvent is removed under reduced pressure, using petrol ether/ethyl acetate as eluant, eluent, silica gel post separation, second
Acid -2- naphthalene ester yields are 99%.1H NMR(400MHz,CDCl3) δ 7.81-7.72 (m, 3H), 7.50 (d, J=2.2Hz, 1H),
7.45-7.37(m,2H),7.19-7.15(m,1H),2.29(s,3H)；13C NMR(101MHz,CDCl3)δ169.7,148.3,
133.7,131.4,129.4,127.8,127.6,126.6,125.7,121.1,118.5,21.2.
Embodiment 2：The synthesis of naphthalen-2-yl hexanoate (3b)
Accurately weigh beta naphthal (72.0mg, 0.5mmol), vinyl caproate (284.4mg, 2.0mmol) and potassium carbonate
(13.8mg, 0.1mmol), and be added sequentially in the Schlenk bottles of 50mL, Isosorbide-5-Nitrae-dioxane (20.0mL) is added, is placed in
10h is reacted in 130 DEG C of oil baths.After reaction, solvent is removed under reduced pressure, using petrol ether/ethyl acetate as eluant, eluent, silica gel
Post separation, caproic acid -2- naphthalene ester yields are 89%.1H NMR(400MHz,CDCl3) δ 7.78-7.70 (m, 3H), 7.47 (d, J=
2.2Hz, 1H), 7.43-7.34 (m, 2H), 7.16-7.12 (m, 1H), 2.51 (dd, J=8.6,6.2Hz, 2H), 1.74 (d, J=
7.4Hz, 2H), 1.00 (t, J=7.4Hz, 3H)；13C NMR(101MHz,CDCl3)δ172.4,148.4,133.8,131.4,
129.4,127.8,127.6,126.5,125.7,121.2,118.5,36.3,18.5,13.7.
Embodiment 3：The synthesis of naphthalen-2-yl pivalate (3c)
Accurately weigh beta naphthal (72.0mg, 0.5mmol), new vinyl acetate acid (128.2mg, 1.0mmol) and hydroxide
Sodium (54.0mg, 0.10mmol), and be added sequentially in the Schlenk bottles of 50mL, ethyl acetate (15.0mL) is added, is placed in 80
30h is reacted in DEG C oil bath.After reaction, solvent is removed under reduced pressure, using petrol ether/ethyl acetate as eluant, eluent, silicagel column
Separation, neopentanoic acid 2- naphthalene ester yields are 86%.1H NMR(400MHz,CDCl3) δ 7.83-7.75 (m, 3H), 7.50 (d, J=
2.1Hz, 1H), 7.48-7.40 (m, 2H), 7.17 (dd, J=8.8,2.3Hz, 1H), 1.38 (s, 9H)；13C NMR(101MHz,
CDCl3)δ177.3,148.8,133.8,131.4,129.3,127.8,127.6,126.5,125.6,121.2,118.4,
39.2,27.2.
Embodiment 4：The synthesis of p-tolyl acetate (3d)
Accurately weigh p-cresol (54.0mg, 0.5mmol), vinyl acetate (86.1mg, 1.0mmol) and potassium hydroxide
(11.2mg, 0.2mmol), and be added sequentially in the Schlenk bottles of 50mL, tetrahydrofuran (2.0mL) is added, is placed in 120 DEG C
18h is reacted in oil bath.After reaction, solvent is removed under reduced pressure, using petrol ether/ethyl acetate as eluant, eluent, silicagel column point
From p-tolyl acetate yield is 98%.1H NMR(400MHz,CDCl3) δ 7.16 (d, J=8.2Hz, 2H), 6.98-6.93
(m,2H),2.33(s,3H),2.27(s,3H)；13C NMR(101MHz,CDCl3)δ169.8,148.5,135.5,130.0,
121.3,21.1,20.9.
Embodiment 5：The synthesis of 4-nitrophenyl acetate (3e)
Accurately weigh p-nitrophenol (69.5mg, 0.5mmol), vinyl acetate (43.0mg, 0.5mmol) and pyridine
(15.8mg, 0.2mmol), and be added sequentially in the Schlenk bottles of 50mL, ethyl alcohol (25.0mL) is added, is placed in 90 DEG C of oil baths
Middle reaction 20h.After reaction, solvent is removed under reduced pressure, using petrol ether/ethyl acetate as eluant, eluent, silica gel post separation, second
Sour p-nitrophenyl ester yield is 91%.1H NMR(400MHz,CDCl3) δ 8.20 (d, J=9.0Hz, 2H), 7.21 (d, J=
9.2Hz,2H),2.28(s,3H)；13C NMR(101MHz,CDCl3)δ168.34,155.3,125.2,122.4,110.0,
21.1.
Embodiment 6：The synthesis of 1,2-phenylene diacetate (3f)
Accurately weigh catechol (55.1mg, 0.5mmol), vinyl acetate (129.1mg, 1.5mmol) and potassium phosphate
(20.1mg, 0.1mmol), and be added sequentially in the Schlenk bottles of 50mL, hexamethylene (8.0mL) is added, is placed in 60 DEG C of oil baths
Middle reaction 26h.After reaction, solvent is removed under reduced pressure, using petrol ether/ethyl acetate as eluant, eluent, silica gel post separation, two
Acetic acid -1,2- phenyl ester yields are 87%.1H NMR(400MHz,CDCl3) δ 7.26-7.21 (m, 2H), 7.18 (dd, J=5.7,
3.7Hz,2H),2.28(s,6H)；13C NMR(101MHz,CDCl3)δ168.3,142.1,126.6,123.5,20.7。
Claims (5)
1. a kind of carboxylic acid aryl esters compounds process for production thereof based on alkenyl carboxylate's ester exchange reaction, with phenolic compound and
Alkenyl carboxylate's class compound is that raw material synthesizes a series of carboxylic acid aryls by the ester exchange reaction of base catalysis alkenyl carboxylate
Ester type compound, which is characterized in that this approach includes the following steps：
Synthetic route is as follows：
Wherein：R1=hydrogen, C1-6Linear or branched alkyl group, hydroxyl, amino, halogen, nitro, cyano, R2=hydrogen, C1-6Straight chain or branch
Alkyl group, aryl, R3=hydrogen, C1-6Linear or branched alkyl group, R4=C1-5Linear or branched alkyl group, phenyl, p-methylphenyl；
(1) phenol, base catalyst, alkenyl carboxylate's class compound and organic solvent are added sequentially in reactor, 25~130 DEG C
Reaction 8~36h hours；The molar ratio of the phenol and alkenyl carboxylate's class compound is 1:1~1:5, phenol and base catalyst rub
You are than being 1:0.01~1:0.5；
(2) after reaction, solvent is removed under reduced pressure, silica gel post separation is carried out with eluant, eluent, obtains carboxylic acid aryl esters compound.
2. prepared by a kind of carboxylic acid aryl esters compound based on alkenyl carboxylate's ester exchange reaction according to claim 1
Method, which is characterized in that this approach includes the following steps：
Wherein：R5For methyl, ethyl or propyl；
(1) naphthols, base catalyst, alkenyl carboxylate's class compound and organic solvent are added sequentially in reactor, 25~130
DEG C reaction 8~36h hours；The molar ratio of the phenol and alkenyl carboxylate's class compound is 1:1~1:5, phenol and base catalyst
Molar ratio is 1:0.01~1:0.5；
(2) after reaction, solvent is removed under reduced pressure, silica gel post separation is carried out with eluant, eluent, obtains carboxylic acid aryl esters compound.
3. a kind of carboxylic acid aryl esters compound based on alkenyl carboxylate's ester exchange reaction according to claim 1 or 2
Preparation method, it is characterised in that：The base catalyst is selected from potassium carbonate, calcium carbonate, sodium carbonate, cesium carbonate, sodium bicarbonate, phosphoric acid
Potassium, potassium dihydrogen phosphate, dipotassium hydrogen phosphate, sodium phosphate, potassium hydroxide, sodium hydroxide, calcium hydroxide, ammonium hydroxide, triethylamine, three fourths
Amine, N, N- diisopropyl ethyl amines, pyridine.
4. a kind of carboxylic acid aryl esters compound based on alkenyl carboxylate's ester exchange reaction according to claim 1 or 2
Preparation method, it is characterised in that：The organic solvent is selected from benzene, toluene, 1,4- dioxane, dimethyl sulfoxide (DMSO), ethyl alcohol, first
Alcohol, the tert-butyl alcohol, isopropanol, dichloromethane, chloroform, n-butyl ether, carbon tetrachloride, dimethyl adipate, ethyl acetate, oil
One kind or several in ether, methyl tertiary butyl ether(MTBE), tetrahydrofuran, acetone, N,N-dimethylformamide, acetonitrile, hexamethylene, n-hexane
Kind.
5. a kind of carboxylic acid aryl esters compound based on alkenyl carboxylate's ester exchange reaction according to claim 1 or 2
Preparation method, it is characterised in that：The amount of the organic solvent is 1~200mL.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110407690A (en) * | 2019-08-21 | 2019-11-05 | 天津利安隆新材料股份有限公司 | A method of benzoic acid phenolic ester class ultraviolet absorbing agent is prepared by transesterification |
| CN114656358A (en) * | 2022-03-28 | 2022-06-24 | 大连理工大学 | Method for preparing ester compound containing olefin under catalysis of deep eutectic solvent |
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| CN102408334A (en) * | 2010-09-21 | 2012-04-11 | 中国科学院福建物质结构研究所 | Method for synthesizing p-fluorophenyl acetate through ester exchange |
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| MANOJ KUMAR等: ""The first vinyl acetate mediated organocatalytic transesterification of phenols: a step towards sustainability"", 《NEW JOURNAL OF CHEMISTRY》 * |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110407690A (en) * | 2019-08-21 | 2019-11-05 | 天津利安隆新材料股份有限公司 | A method of benzoic acid phenolic ester class ultraviolet absorbing agent is prepared by transesterification |
| CN110407690B (en) * | 2019-08-21 | 2022-05-31 | 天津利安隆新材料股份有限公司 | Method for preparing benzoic acid phenol ester ultraviolet absorbent through ester exchange |
| CN114656358A (en) * | 2022-03-28 | 2022-06-24 | 大连理工大学 | Method for preparing ester compound containing olefin under catalysis of deep eutectic solvent |
| CN114656358B (en) * | 2022-03-28 | 2023-02-14 | 大连理工大学 | Method for preparing ester compound containing olefin under catalysis of deep eutectic solvent |
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Application publication date: 20180904 |