CN116143621A - Method for preparing benzoate compound by using boron salt catalytic activated amide - Google Patents
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- CN116143621A CN116143621A CN202211619100.3A CN202211619100A CN116143621A CN 116143621 A CN116143621 A CN 116143621A CN 202211619100 A CN202211619100 A CN 202211619100A CN 116143621 A CN116143621 A CN 116143621A
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- 238000000034 method Methods 0.000 title claims abstract description 25
- -1 benzoate compound Chemical class 0.000 title claims abstract description 16
- 150000001638 boron Chemical class 0.000 title claims abstract description 15
- 150000001408 amides Chemical class 0.000 title claims abstract description 14
- 230000003197 catalytic effect Effects 0.000 title description 4
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims abstract description 8
- 150000003936 benzamides Chemical class 0.000 claims abstract description 7
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 7
- 238000006136 alcoholysis reaction Methods 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical class [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052796 boron Inorganic materials 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 34
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical group FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 14
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 abstract description 2
- 239000000575 pesticide Substances 0.000 abstract description 2
- 125000005233 alkylalcohol group Chemical group 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000004809 thin layer chromatography Methods 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- FEXQDZTYJVXMOS-UHFFFAOYSA-N Isopropyl benzoate Chemical compound CC(C)OC(=O)C1=CC=CC=C1 FEXQDZTYJVXMOS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- RQVWTMCUTHKGCM-UHFFFAOYSA-N S-Methyl benzenecarbothioate Chemical compound CSC(=O)C1=CC=CC=C1 RQVWTMCUTHKGCM-UHFFFAOYSA-N 0.000 description 2
- UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000006249 magnetic particle Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000007056 transamidation reaction Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/18—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group
- C07C67/20—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from amides or lactams
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/26—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to carbon atoms of six-membered aromatic rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for preparing benzoate compounds by using boron salt-catalyzed activated amide takes benzamide compounds and alkyl alcohol as raw materials in an air environment, and the target ester compounds are obtained by alcoholysis of the benzamide compounds and high yield under the catalysis of boron salt. The method can realize the synthesis of a series of benzoate compounds with high yield under mild conditions, does not need to additionally add other reagents, has the advantages of environmental friendliness, high atom economy and simple and convenient post-treatment, and has wide application potential in the fields of medicines, pesticides, foods, dyes, solvents and the like.
Description
Technical Field
The invention belongs to the fields of organic chemical industry, organic synthesis and boron salt catalysis, relates to preparation of aryl ester compounds, and in particular relates to a method for generating benzoate compounds by reacting benzamide compounds with alcohol under the catalysis of boron salt.
Background
The ester compounds are widely applied to plants, animals and microorganisms, have flower fragrance, fruit fragrance, wine fragrance or honey fragrance, and are widely applied to the fields of medicines, pesticides, foods, dyes, solvents and the like. There are many methods for synthesizing ester compounds at present, wherein the classical synthesis method is to condense carboxylic acid and its derivative with alcohol, and metal catalysis C-H bond activation and transesterification are effective methods for preparing ester compounds. Although these synthetic methods have many advantages of their own, each also has certain limitations such as: metal catalysts, condensing agents, the production of unwanted by-products, etc. are required. These disadvantages do not meet the concept of green synthesis and are difficult to adapt to the requirements of industrial production. Thus, synthetic research on the development of green clean synthetic ester compounds has been a hotspot in the field of organic chemistry.
Amides are a widely used class of organic synthons in organic synthesis, where the amide group can be converted to other functional groups, such as ester groups, carboxyl groups, and the like. However, due to the high stability of the amide, its conversion to other functional groups generally requires multiple steps of reactions and harsh conditions. In recent years, direct conversion of amides has attracted considerable attention, whereby a number of mild and practical transamidation processes have been developed, such as: the method comprises the steps of in-situ activation of amide by using equivalent tricarboxylic anhydride, conversion of amide into ester compound by a one-pot method, and nickel catalytic activation of C-N bond of amide, so that N-phenyl benzamide is directly converted into aromatic ester.
At present, a method for synthesizing esters by taking amide as a raw material has been reported, and considerable results are obtained, but the method still has certain difficulty for a method for converting thioarylamides compounds into esters. Based on the above, it is very necessary to construct a green, novel and universal alcoholysis method of amide compounds.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a method for preparing benzoate compounds by using boron salt as a catalyst by catalyzing and activating amide with boron salt.
In order to achieve the above purpose, the invention adopts the following technical scheme: a method for preparing benzoate compounds by using boron salt catalytic activated amide comprises the steps of taking benzamide compounds of a formula I and alcohol as raw materials in an air environment, and generating benzoate compounds by alcoholysis of the benzamide compounds under the catalysis of boron salt, wherein the reaction formula is as follows:
wherein R is 1 Is a hydrogen atom, X is O or S; r is alkyl.
Preferably, R is C 1 -C 4 Preferably ethyl, propyl or butyl.
Preferably, the boron salt catalyst is boron trifluoride diethyl etherate.
The adding amount of the boron salt catalyst at the initial time of the reaction is 2 times of that of the benzamide compound according to the mole ratio; the molar ratio of the amide compound to the alcohol at the beginning of the reaction is 1:10. the reaction is carried out at a temperature of 80 ℃ and no solvent is required for the reaction.
The invention provides a green, economical and practical synthesis method of an aryl ester compound with universality. The method prepares the ester compound by alcoholysis of amide under the catalysis of boron salt. The method is green and novel, has good substrate adaptability and does not have the participation of metal catalysts and ligands.
Detailed Description
The following examples will aid in the understanding of the present invention, but the content of the present invention is not limited thereto.
EXAMPLE 1 preparation of Ethyl benzoate
A reaction tube of 10mL was placed in a magnet, and under air conditions, the substrate benzamide (60.5 mg,0.5 mmol), boron trifluoride diethyl etherate (141.9 mg,1.0 mmol), ethanol (0.5 mL) were added sequentially. The reaction tube was then placed in an oil bath at 80 ℃ for reaction, and the reaction was monitored by Thin Layer Chromatography (TLC) until the reaction was complete. The reaction product was concentrated by rotary evaporator with ethyl acetate andpetroleum ether (ethyl acetate/petroleum ether=1:3) is used as eluent and is separated and purified by silica gel column chromatography, finally the target product ethyl benzoate (74.6 mg) is obtained, the product is colorless oily liquid, the yield is 99.5%, and the structural formula is that
1 H NMR(400MHz,CDCl 3 )：δ8.07(dd,J＝8.2,1.5Hz,2H),7.63–7.50(m,1H),7.45(t,J＝7.6Hz,2H),4.40(q,J＝7.1Hz,2H),1.41(t,J＝7.2Hz,3H)ppm.
13 C NMR(101MHz,CDCl 3 )：δ166.68,132.85,130.57,129.58,128.36,61.00,14.39ppm.
MS:m/z,found:150.18。
EXAMPLE 2 preparation of propyl benzoate
A10 mL reaction tube was placed in a magnet, and under air conditions, substrate benzamide (60.5 mg,0.5 mmol), boron trifluoride diethyl etherate (141.9 mg,1.0 mmol), and propanol (0.5 mL) were added sequentially. The reaction tube was then placed in an oil bath at 80 ℃ for reaction, and the reaction was monitored by Thin Layer Chromatography (TLC) until the reaction was complete. Concentrating the reaction product by rotary evaporator, separating and purifying by silica gel column chromatography with ethyl acetate and petroleum ether (ethyl acetate/petroleum ether=1:3) as eluent to obtain target product propyl benzoate (80.7 mg), which is colorless oily liquid, with yield of 98.3%, and structural formula of
1 H NMR(400MHz,CDCl 3 )：δ8.15–7.98(m,2H),7.61–7.52(m,1H),7.45(dd,J＝8.4,7.1Hz,2H),4.30(t,J＝6.7Hz,2H),1.82(p,J＝7.1Hz,2H),1.05(t,J＝7.5Hz,3H)ppm.
13 C NMR(101MHz,CDCl 3 )：δ166.70,132.83,130.58,129.57,128.35,66.56,22.18,10.56ppm.
MS:m/z,found:164.20。
EXAMPLE 3 preparation of isopropyl benzoate
Take 10A reaction tube mL was placed in a magnetic particle, and under air conditions, the substrate benzamide (60.5 mg,0.5 mmol), boron trifluoride diethyl etherate (141.9 mg,1.0 mmol), and isopropyl alcohol (0.5 mL) were added sequentially. The reaction tube was then placed in an oil bath at 80℃for 4h. The reaction was monitored by Thin Layer Chromatography (TLC) until completion, the reaction product was concentrated by rotary evaporator, and purified by silica gel column chromatography using ethyl acetate and petroleum ether (ethyl acetate/petroleum ether=1:3) as eluent to finally obtain the target product isopropyl benzoate (80.4 mg), the product was a colorless oily liquid with a yield of 98.1%, the structural formula was
1 H NMR(400MHz,CDCl 3 )：δ8.07(dd,J＝8.2,1.4Hz,2H),7.61–7.52(m,1H),7.45(t,J＝7.6Hz,2H),5.28(m,1H),1.40(d,J＝6.4Hz,6H)ppm.
13 C NMR(101MHz,CDCl 3 )：δ166.21,132.78,131.01,129.59,128.35,68.43,22.05ppm.
MS:m/z,found:164.20。
EXAMPLE 4 preparation of n-butyl benzoate
A reaction tube of 10mL was placed in a magnet, and under air conditions, substrate benzamide (60.5 mg,0.5 mmol), boron trifluoride diethyl etherate (141.9 mg,1.0 mmol), and n-butanol (0.5 mL) were added sequentially. The reaction tube was then placed in an oil bath at 80 ℃ for reaction, and the reaction was monitored by Thin Layer Chromatography (TLC) until the reaction was complete. The reaction product was concentrated by rotary evaporator, and purified by silica gel column chromatography using ethyl acetate and petroleum ether (ethyl acetate/petroleum ether=1:3) as eluent to obtain the target product n-butyl benzoate (86.5 mg), the product was colorless oily liquid, the yield was 97.2%, and the structural formula was
1 H NMR(400MHz,CDCl 3 )：δ8.14–7.97(m,2H),7.65–7.52(m,1H),7.48–7.39(m,2H),4.35(t,J＝6.6Hz,2H),1.77(m,2H),1.59–1.39(m,2H),1.00(t,J＝7.4Hz,3H)ppm.
13 C NMR(101MHz,CDCl 3 )：δ166.73,132.84,130.59,129.59,128.37,64.88,30.86,19.36,13.84ppm.
MS:m/z,found:178.23。
EXAMPLE 5 preparation of methyl thiobenzoate
A reaction tube of 10mL was placed in a magnet, and under air conditions, the substrate thiobenzamide (68.6 mg,0.5 mmol), boron trifluoride diethyl etherate (141.9 mg,1.0 mmol), and n-butanol (0.5 mL) were added sequentially. The reaction tube was then placed in an oil bath at 80℃for 4h. The reaction was monitored by Thin Layer Chromatography (TLC) until completion, the reaction product was concentrated by rotary evaporator, and purified by silica gel column chromatography using ethyl acetate and petroleum ether (ethyl acetate/petroleum ether=1:3) as eluent to finally obtain the target product methyl thiobenzoate (75.7 mg), the product was a yellow oily liquid with a yield of 99.6% and a structural formula of
1 H NMR(400MHz,CDCl 3 )：δ8.07–8.00(m,2H),7.54(td,J＝7.3,1.5Hz,1H),7.43(t,J＝7.8Hz,2H),3.91(s,3H)ppm.
13 C NMR(101MHz,CDCl 3 )：δ167.19,132.99,130.24,129.65,128.43,52.17ppm.
MS:m/z,found:152.21。
Claims (7)
1. A method for preparing benzoate compounds by using boron salt-catalyzed activated amide is characterized in that in an air environment, benzamide compounds with a formula I and alcohol are taken as raw materials, and the benzamide compounds are subjected to alcoholysis under the catalysis of boron salt to generate the benzoate compounds, wherein the reaction formula is as follows:
wherein R is 1 Is a hydrogen atom, X is O or S;r is alkyl.
2. The method of claim 1, wherein R is C 1 -C 4 Is a hydrocarbon group.
3. The method of claim 2, wherein R is ethyl, propyl, or butyl.
4. A process according to any one of claims 1 to 3, wherein the boron salt catalyst is boron trifluoride etherate.
5. A process according to any one of claims 1 to 3, wherein the reaction temperature is 80 ℃.
6. A method according to any one of claims 1 to 3, wherein the boron salt catalyst is added in a molar ratio of 2 times that of the benzamide compound at the beginning of the reaction.
7. A process according to any one of claims 1 to 3, wherein the reaction is initiated with a molar ratio of benzamide compound to alcohol of 1:10.
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