CN113461510A - 一种芳香酸类化合物及其制备方法 - Google Patents
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- -1 Aromatic acid compound Chemical class 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title abstract description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 17
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims abstract description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 3
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
- 239000012043 crude product Substances 0.000 claims abstract description 3
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 159000000032 aromatic acids Chemical class 0.000 claims description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000047 product Substances 0.000 abstract description 15
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 125000004429 atom Chemical group 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
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- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000003321 amplification Effects 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000003199 nucleic acid amplification method Methods 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 81
- 238000001228 spectrum Methods 0.000 description 44
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 26
- 229910052799 carbon Inorganic materials 0.000 description 26
- 229910052739 hydrogen Inorganic materials 0.000 description 26
- 239000001257 hydrogen Substances 0.000 description 26
- 239000007787 solid Substances 0.000 description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 25
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 238000012512 characterization method Methods 0.000 description 13
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 10
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 10
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 8
- VPHHJAOJUJHJKD-UHFFFAOYSA-N 3,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(Cl)=C1 VPHHJAOJUJHJKD-UHFFFAOYSA-N 0.000 description 5
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 5
- ADCUEPOHPCPMCE-UHFFFAOYSA-N 4-cyanobenzoic acid Chemical compound OC(=O)C1=CC=C(C#N)C=C1 ADCUEPOHPCPMCE-UHFFFAOYSA-N 0.000 description 5
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 description 5
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 5
- REIDAMBAPLIATC-UHFFFAOYSA-M 4-methoxycarbonylbenzoate Chemical compound COC(=O)C1=CC=C(C([O-])=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-M 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
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- 238000005286 illumination Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 5
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 3
- 238000003912 environmental pollution Methods 0.000 description 3
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 2
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
- FVJIUQSKXOYFKG-UHFFFAOYSA-N (3,4-dichlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C(Cl)=C1 FVJIUQSKXOYFKG-UHFFFAOYSA-N 0.000 description 1
- PTHGDVCPCZKZKR-UHFFFAOYSA-N (4-chlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C=C1 PTHGDVCPCZKZKR-UHFFFAOYSA-N 0.000 description 1
- GEZMEIHVFSWOCA-UHFFFAOYSA-N (4-fluorophenyl)methanol Chemical compound OCC1=CC=C(F)C=C1 GEZMEIHVFSWOCA-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 1
- JJCKHVUTVOPLBV-UHFFFAOYSA-N 3-Methylbenzyl alcohol Chemical compound CC1=CC=CC(CO)=C1 JJCKHVUTVOPLBV-UHFFFAOYSA-N 0.000 description 1
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
- XAASLEJRGFPHEV-UHFFFAOYSA-N 4-cyanobenzyl alcohol Chemical compound OCC1=CC=C(C#N)C=C1 XAASLEJRGFPHEV-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- KMTDMTZBNYGUNX-UHFFFAOYSA-N 4-methylbenzyl alcohol Chemical compound CC1=CC=C(CO)C=C1 KMTDMTZBNYGUNX-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 1
- VBWFYEFYHJRJER-UHFFFAOYSA-N methyl 4-(hydroxymethyl)benzoate Chemical compound COC(=O)C1=CC=C(CO)C=C1 VBWFYEFYHJRJER-UHFFFAOYSA-N 0.000 description 1
- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- SEVSMVUOKAMPDO-UHFFFAOYSA-N para-Acetoxybenzaldehyde Natural products CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 1
- VEDDBHYQWFOITD-UHFFFAOYSA-N para-bromobenzyl alcohol Chemical compound OCC1=CC=C(Br)C=C1 VEDDBHYQWFOITD-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ZPHGMBGIFODUMF-UHFFFAOYSA-N thiophen-2-ylmethanol Chemical compound OCC1=CC=CS1 ZPHGMBGIFODUMF-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
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- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
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Abstract
一种芳香酸类化合物及其制备方法,涉及化合物合成技术领域,其结构式为:。其中,R1、R2、R3、R4、R5为甲基、甲氧基、溴基、氯基、氟基、酯基、氰基、甲硫基、氢原子中的一种,其制备方法是将芳香醇、芳香醛类化合物溶于反应溶剂,在室温360‑450 nm光源照射下,敞开搅拌反应2‑8 h,反应结束后,减压抽出溶剂,对所得粗产品重结晶即可得到芳香酸类化合物,反应溶剂包括乙酸乙酯、丙酮、乙醚、二氯甲烷、四氢呋喃、乙二醇二乙醚、二丙二醇二甲醚、乙二醇二甲醚、二氧六环中的一种或多种。本发明可简化工艺过程、降低生产成本和对环境的污染,且其原子经济性高、反应工艺条件稳定、无需使用有机金属催化剂、产品易于纯化,极为适宜工业化放大生产。
Description
技术领域
本发明涉及化合物合成技术领域,尤其指一种芳香酸类化合物及其制备方法。
背景技术
芳香酸类化合物是一类重要的化工产品,其主要结构单元在农药、医药等行业非常常见。目前,已报道的大多数芳香酸的合成路线涉及步骤较多,存在原子经济性低、生产成本昂贵、副产物较多和环境污染严重等缺点。由芳香醇或醛制备芳香酸往往需要经过氧化和酸化两步,且使用过渡金属催化剂及化学计量的强碱以促进反应完成。这导致了环境污染大、成本高昂且使得进一步的直接转化难以实现。
发明内容
本发明的目的之一在于提供一种芳香酸类化合物的制备方法,以简化工艺过程、降低生产成本和对环境的污染。
为了解决上述技术问题,本发明采用如下技术方案:一种芳香酸类化合物及,其结构式为:
其中,R1、R2、R3、R4、R5为甲基、甲氧基、溴基、氯基、氟基、酯基、氰基、甲硫基、氢原子等基团中的一种。
上述芳香酸类化合物的制备方法包括以下步骤:将芳香醇、芳香醛类化合物溶于反应溶剂,在室温360-450 nm光源照射下,敞开搅拌反应2-8 h,反应结束后,减压抽出溶剂,对所得粗产品重结晶即可得到所述芳香酸类化合物,所述反应溶剂包括乙酸乙酯、丙酮、乙醚、二氯甲烷、四氢呋喃、乙二醇二乙醚、二丙二醇二甲醚、乙二醇二甲醚、二氧六环中的一种或多种。
优选地,所述芳香醇、芳香醛类化合物与所述反应溶剂的比例为0.1 g : 0.5-10ml。
更优选地,所述芳香醇、芳香醛类化合物与所述反应溶剂的摩尔比是1 : 0.1-200。
更优选地,所述芳香醇、芳香醛类化合物与所述反应溶剂可在空气中或者纯氧条件下进行反应。
更优选地,所述搅拌反应中的搅拌速度为100-600转/分。
本发明的有益效果在于:通过在室温光照条件下,敞开搅拌完成反应,整个反应可直接利用空气中的氧气或者利用纯氧作为氧化剂和氧源制备芳香酸化合物,操作简单,并且所使用溶剂易于回收,与现有的制备方法相比,该方法具有反应条件温和、降低对环境的污染、原子经济性高、反应周期短、反应工艺条件稳定、无需使用有机金属催化剂、成本低、后处理简单、产品易于纯化、操作简便安全的优点,极为适宜工业化放大生产。
附图说明
图1为本发明实施例1中制备得到的产物的核磁氢谱及碳谱图;
图2为本发明实施例2中制备得到的产物的核磁氢谱及碳谱图;
图3为本发明实施例3中制备得到的产物的核磁氢谱及碳谱图;
图4为本发明实施例4中制备得到的产物的核磁氢谱、碳谱及氟谱图;
图5为本发明实施例5中制备得到的产物的核磁氢谱及碳谱图;
图6为本发明实施例6中制备得到的产物的核磁氢谱及碳谱图;
图7为本发明实施例7中制备得到的产物的核磁氢谱及碳谱图;
图8为本发明实施例8中制备得到的产物的核磁氢谱及碳谱图;
图9为本发明实施例9中制备得到的产物的核磁氢谱及碳谱图;
图10为本发明实施例10中制备得到的产物的核磁氢谱及碳谱图;
图11为本发明实施例11中制备得到的产物的核磁氢谱及碳谱图;
图12为本发明实施例12中制备得到的产物的核磁氢谱及碳谱图;
图13为本发明实施例13中制备得到的产物的核磁氢谱及碳谱图。
具体实施方式
为了便于本领域技术人员的理解,下面结合实施例与附图对本发明作进一步的说明,实施方式提及的内容并非对本发明的限定。需要提前说明的是,以下实施例是在实验室完成的,本领域技术人员应当明白,实施例中给出的各组分用量仅代表了各组分之间的配比关系,而非具体的限定。
下述各实施例均是通过本发明提供的制备方法制备得到的相应的芳香酸类化合物。
实施例1
苯甲酸:
1、苯甲酸的制备路线如下所示:
具体操作过程为:在25 ml圆底烧瓶中依次加入苯甲醇或苯甲醛(4 mmol),丙酮(10ml),于室温下385nm波长光照敞开体系搅拌5h,停止反应,然后真空减压回收溶剂,并对剩余固体重结晶,得到白色固体0.45g,收率92.3 %。
2、苯甲酸的表征:
如图1所示,制备得到的苯甲酸的核磁氢谱图中1H NMR (400 MHz, DMSO) δ12.97 (s, 1 H), 7.96 - 7.93 (m, 2 H), 7.65 - 7.60 (m, 1 H), 7.52 - 7.48 (m, 2H);核磁碳谱图中13C NMR (100 MHz, DMSO) δ 167.8, 133.4, 131.2, 129.8, 129.1,可见该结果表明成功制备了高纯度的苯甲酸。
实施例2
对甲基苯甲酸:
1、对甲基苯甲酸的制备路线如下所示:
具体操作过程为:在25 ml圆底烧瓶中依次加入对甲基苯甲醇或对甲基苯甲醛(4mmol),乙二醇二乙醚(5ml),室温下380nm波长光照敞开体系搅拌3h,停止反应,真空减压回收溶剂,剩余固体重结晶,得到白色固体0.51g,收率94 %。
2、对甲基苯甲酸的表征:
如图2所示,制备得到的对甲基苯甲酸的核磁氢谱图中1H NMR (400 MHz, DMSO)δ 12.80 (s, 1 H), 7.83 (d, J = 8.0 Hz, 2 H), 7.30 (d, J = 8.0 Hz, 2 H), 2.36(s, 3 H) ;核磁碳谱图中13C NMR (100 MHz, DMSO) δ 167.8, 143.6, 129.9, 129.7,128.5, 21.7,可见该结果表明成功制备了高纯度的对甲基苯甲酸。
实施例3
对甲氧基苯甲酸:
1、对甲氧基苯甲酸的制备路线如下所示:
具体操作过程为:在25 ml圆底烧瓶中依次加入对甲氧基苯甲醇或对甲氧基苯甲醛(4 mmol),乙二醇二乙醚(5ml),室温下385nm波长光照敞开体系搅拌2h,停止反应,真空减压回收溶剂,剩余固体重结晶,得到白色固体0.57g,收率93 %。
2、对甲氧基苯甲酸的表征:
如图3所示,制备得到的对甲氧基苯甲酸的核磁氢谱图中1H NMR (400 MHz,DMSO) δ 12.64 (s, 1 H), 7.89 (d, J = 8.8 Hz, 2 H), 7.02 (d, J = 8.8 Hz, 2 H),3.82 (s, 3 H) ;核磁碳谱图中13C NMR (100 MHz, DMSO) δ 167.5, 163.3, 131.8,123.5, 114.3, 55.9,可见该结果表明成功制备了高纯度的对甲氧基苯甲酸。
实施例4
对氟苯甲酸:
1、对氟苯甲酸的制备路线如下所示:
具体操作过程为:在25 ml圆底烧瓶中依次加入对氟苯甲醇或对氟苯甲醛(4mmol),丙酮(5ml),室温下395nm波长光照敞开体系搅拌5h,停止反应,真空减压回收溶剂,剩余固体重结晶,得到灰白色固体0.52g,收率92 %。
2、对氟苯甲酸的表征:
如图4所示,制备得到的对氟苯甲酸的核磁氢谱图中1H NMR (400 MHz, DMSO) δ13.07 (s, 1 H), 8.03 - 7.98 (m, 2 H), 7.35 - 7.29 (m, 2 H) ;核磁碳谱图中13CNMR (100 MHz, DMSO) δ 166.9, 165.4 (d, J = 249.1 Hz), 132.7 (d, J = 9.4 Hz),127.9, 116.1 (d, J = 21.9 Hz) ;核磁氟谱图中19F NMR (376 MHz, DMSO) δ -106.9,可见该结果表明成功制备了高纯度的对氟苯甲酸。
实施例5
对氯苯甲酸:
1、对氯苯甲酸的制备路线如下所示:
具体操作过程为:在25 ml圆底烧瓶中依次加入对氯苯甲醇或对氯苯甲醛(4mmol),丙酮(5ml),室温下395nm波长光照敞开体系搅拌5h,停止反应,真空减压回收溶剂,剩余固体重结晶,得到白色固体0.59g,收率95 %。
2、对氯苯甲酸的表征:
如图5所示,制备得到的对氯苯甲酸的核磁氢谱图中1H NMR (400 MHz, DMSO) δ13.20 (s, 1 H), 7.94 (d, J = 8.8 Hz, 2 H), 7.57 (d, J = 8.4 Hz, 2 H);核磁碳谱图中13C NMR (100 MHz, DMSO) δ 167.0, 138.3, 131.7, 130.1, 129.3,可见该结果表明成功制备了高纯度的对氯苯甲酸。
实施例6
对溴苯甲酸:
1、对溴苯甲酸的制备路线如下所示:
具体操作过程为:在25 ml圆底烧瓶中依次加入对溴苯甲醇或对溴苯甲醛(4mmol),丙酮(5ml),室温下395nm波长光照敞开体系搅拌5h,停止反应,真空减压回收溶剂,剩余固体重结晶,得到白色固体0.75g,收率93 %。
2、对溴苯甲酸的表征:
如图6所示,制备得到的对溴苯甲酸的核磁氢谱图中1H NMR (400 MHz, DMSO) δ13.21 (s, 1 H), 7.86 (d, J = 8.4 Hz, 2 H), 7.71 (d, J = 8.4 Hz, 2 H);核磁碳谱图中13C NMR (100 MHz, DMSO) δ 167.1, 132.2, 131.8, 130.5, 127.4,可见该结果表明成功制备了高纯度的对溴苯甲酸。
实施例7
对氰基苯甲酸:
1、对氰基苯甲酸的制备路线如下所示:
具体操作过程为:在25 ml圆底烧瓶中依次加入对氰基苯甲醇或对氰基苯甲醛(4mmol),丙酮(10ml),室温下400nm波长光照敞开体系搅拌8h,停止反应,真空减压回收溶剂,剩余固体重结晶,得到灰白色固体0.54g,收率92 %。
2、对氰基苯甲酸的表征:
如图7所示,制备得到的对氰基苯甲酸的核磁氢谱图中1H NMR (400 MHz, DMSO)δ 13.60 (s, 1 H), 8.06 (s, 2 H), 8.01 (s, 2 H);核磁碳谱图中13C NMR (100 MHz,DMSO) δ 133.6, 118.7, 115.5,可见该结果表明成功制备了高纯度的对氰基苯甲酸。
实施例8
3,4-二氯苯甲酸:
1、3,4-二氯苯甲酸的制备路线如下所示:
具体操作过程为:在25 ml圆底烧瓶中依次加入3,4-二氯苯甲醇或3,4-二氯苯甲醛(4 mmol),丙酮(10ml),室温下400nm波长光照敞开体系搅拌6h,停止反应,真空减压回收溶剂,剩余固体重结晶,得到白色固体0.71g,收率93 %。
2、3,4-二氯苯甲酸的表征:
如图8所示,制备得到的3,4-二氯苯甲酸的核磁氢谱图中1H NMR (400 MHz,DMSO) δ 13.51 (s, 1 H), 8.06 (d, J = 2.0 Hz, 1 H), 7.88 (dd, J = 8.4, 1.8 Hz,1 H), 7.77 (d, J = 8.4 Hz, 1 H);核磁碳谱图中13C NMR (100 MHz, DMSO) δ 165.9,136.3, 132.0, 131.9, 131.6, 131.5, 129.8,可见该结果表明成功制备了高纯度的3,4-二氯苯甲酸。
实施例9
2-呋喃甲酸:
1、2-呋喃甲酸的制备路线如下所示:
具体操作过程为:在25 ml圆底烧瓶中依次加入2-呋喃甲醇或2-呋喃甲醛(4mmol),丙酮(10ml),室温下385nm波长光照氧气氛下搅拌6h,停止反应,真空减压回收溶剂,剩余固体重结晶,得到灰白色固体0.42g,收率94 %。
2、2-呋喃甲酸的表征:
如图9所示,制备得到的2-呋喃甲酸的核磁氢谱图中1H NMR (400 MHz, DMSO) δ13.07 (s, 1 H), 7.91 (s, 1 H), 7.21 (d, J = 3.2 Hz, 1 H), 6.65 - 6.64 (m, 1H);核磁碳谱图中13C NMR (100 MHz, DMSO) δ 159.8, 147.6, 145.4, 118.2, 112.6,可见该结果表明成功制备了高纯度的2-呋喃甲酸。
实施例10
2-噻吩甲酸:
1、2-噻吩甲酸的制备路线如下所示:
具体操作过程为:在25 ml圆底烧瓶中依次加入2-噻吩甲醇或2-噻吩甲醛(4mmol),丙酮(10ml),室温下385nm波长光照氧气氛下搅拌6h,停止反应,真空减压回收溶剂,剩余固体重结晶,得到灰白色固体0.47g,收率92 %。
2、2-噻吩甲酸的表征:
如图10所示,制备得到的2-噻吩甲酸的核磁氢谱图中1H NMR (400 MHz, DMSO) δ13.06 (s, 1 H), 7.88 (dd, J = 5.2, 1.2 Hz, 1 H), 7.73 (dd, J = 3.6, 1.2 Hz, 1H), 7.18 (dd, J = 5.0, 4.0 Hz, 1 H);核磁碳谱图中13C NMR (100 MHz, DMSO) δ163.4, 135.2, 133.8, 133.7, 128.8,可见该结果表明成功制备了高纯度的2-噻吩甲酸。
实施例11
对苯二甲酸单甲酯:
1、对苯二甲酸单甲酯的制备路线如下所示:
具体操作过程为:在25 ml圆底烧瓶中依次加入4-羟甲基苯甲酸甲酯或4-甲酰基苯甲酸甲酯(4 mmol),丙酮(10ml),室温下390nm波长光照氧气氛下搅拌7h,停止反应,真空减压回收溶剂,剩余固体重结晶,得到白色固体0.68g,收率95 %。
2、对苯二甲酸单甲酯的表征:
如图11所示,制备得到的对苯二甲酸单甲酯的核磁氢谱图中1H NMR (400 MHz,DMSO) δ 13.37 (s, 1 H), 8.06 (s, 4 H), 3.88 (s, 3 H);核磁碳谱图中13C NMR (100MHz, DMSO) δ 167.1, 166.1, 135.3, 133.7, 130.1, 129.9, 53.0,可见该结果表明成功制备了高纯度的对苯二甲酸单甲酯。
实施例12
3-甲基苯甲酸:
1、3-甲基苯甲酸的制备路线如下所示:
具体操作过程为:在25 ml圆底烧瓶中依次加入间甲基苯甲醇或间甲基苯甲醛(4mmol),乙二醇二乙醚(5ml),室温下385nm波长光照敞开体系搅拌4h,停止反应,真空减压回收溶剂,剩余固体重结晶,得到淡黄色固体0.50g,收率92 %。
2、3-甲基苯甲酸的表征:
如图12所示,制备得到的3-甲基苯甲酸的核磁氢谱图中1H NMR (400 MHz, DMSO)δ 12.88 (s, 1 H), 7.76 (s, 1 H), 7.74 (d, J = 7.6 Hz, 1 H), 7.44 - 7.36 (m, 2H), 2.36 (s, 3 H);核磁碳谱图中13C NMR (100 MHz, DMSO) δ 167.9, 138.4, 134.0,131.2, 130.2, 129.0, 127.0, 21.3,可见该结果表明成功制备了高纯度的3-甲基苯甲酸。
实施例13
2-甲基苯甲酸:
1、2-甲基苯甲酸的制备路线如下所示:
具体操作过程为:在25 ml圆底烧瓶中依次加入2-甲基苯甲醇或2-甲基苯甲醛(4mmol),乙二醇二乙醚(5ml),室温下385nm波长光照敞开体系搅拌8h,停止反应,真空减压回收溶剂,剩余固体重结晶,得到白色固体0.49g,收率91 %。
2、2-甲基苯甲酸的表征:
如图13所示,制备得到的2-甲基苯甲酸的核磁氢谱图中1H NMR (400 MHz, DMSO)δ 12.82 (s, 1 H), 7.81 (d, J = 7.6 Hz, 1 H), 7.46 - 7.41 (m, 1 H), 7.28 (t, J= 8.4 Hz, 2 H), 2.51 (s, 3 H);核磁碳谱图中13C NMR (100 MHz, DMSO) δ 169.2,139.5, 132.2, 132.0, 130.9, 130.7, 126.4, 21.8,可见该结果表明成功制备了高纯度的2-甲基苯甲酸。
上述实施例为本发明较佳的实现方案,除此之外,本发明还可以其它方式实现,在不脱离本技术方案构思的前提下任何显而易见的替换均在本发明的保护范围之内。
Claims (6)
2.权利要求1所述的芳香酸类化合物的制备方法,其特征在于,包括以下步骤:将芳香醇、芳香醛类化合物溶于反应溶剂,在室温360-450 nm光源照射下,敞开搅拌反应2-8 h,反应结束后,减压抽出溶剂,对所得粗产品重结晶即可得到所述芳香酸类化合物,所述反应溶剂包括乙酸乙酯、丙酮、乙醚、二氯甲烷、四氢呋喃、乙二醇二乙醚、二丙二醇二甲醚、乙二醇二甲醚、二氧六环中的一种或多种。
3.根据权利要求2所述的制备方法,其特征在于:所述芳香醇、芳香醛类化合物与所述反应溶剂的比例为0.1 g : 0.5-10 ml。
4.根据权利要求2所述的制备方法,其特征在于:所述芳香醇、芳香醛类化合物与所述反应溶剂的摩尔比是1 : 0.1-200。
5.根据权利要求2-4中任一项所述的制备方法,其特征在于:所述芳香醇、芳香醛类化合物与所述反应溶剂可在空气中或者纯氧条件下进行反应。
6.根据权利要求2-4中任一项所述的制备方法,其特征在于:所述搅拌反应中的搅拌速度为100-600转/分。
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CN114315556A (zh) * | 2021-12-28 | 2022-04-12 | 上海应用技术大学 | 一种芳香酸的制备方法 |
CN114956968A (zh) * | 2022-01-05 | 2022-08-30 | 东华理工大学 | 一种羰基化合物的制备方法 |
CN114956968B (zh) * | 2022-01-05 | 2023-10-27 | 东华理工大学 | 一种羰基化合物的制备方法 |
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