CN102432442B - 一种缩醛的制备方法 - Google Patents
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- 238000002360 preparation method Methods 0.000 title abstract description 7
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 title abstract description 5
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- CMPNPRUFRJFQIB-UHFFFAOYSA-N [N].[Cu] Chemical class [N].[Cu] CMPNPRUFRJFQIB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- -1 trimethyl silicon nitrile Chemical class 0.000 claims abstract description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000004440 column chromatography Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 16
- UHIJLWIHCPPKOP-UHFFFAOYSA-N [N].[Zn] Chemical compound [N].[Zn] UHIJLWIHCPPKOP-UHFFFAOYSA-N 0.000 claims description 10
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 10
- 238000010189 synthetic method Methods 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 4
- 239000011701 zinc Substances 0.000 abstract description 4
- 239000003208 petroleum Substances 0.000 abstract description 2
- HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 abstract 1
- OKBMTBGUGSCQKB-UHFFFAOYSA-N [N].[Zn].C1(=CC=CC=C1)C(C)N Chemical compound [N].[Zn].C1(=CC=CC=C1)C(C)N OKBMTBGUGSCQKB-UHFFFAOYSA-N 0.000 abstract 1
- 150000001241 acetals Chemical class 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000013904 zinc acetate Nutrition 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- BEAZKUGSCHFXIQ-UHFFFAOYSA-L zinc;diacetate;dihydrate Chemical compound O.O.[Zn+2].CC([O-])=O.CC([O-])=O BEAZKUGSCHFXIQ-UHFFFAOYSA-L 0.000 description 2
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 1
- 0 CC(*)c1ccccc1 Chemical compound CC(*)c1ccccc1 0.000 description 1
- 238000005773 Enders reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011941 photocatalyst Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000247 postprecipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
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- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
一种缩醛的制备方法，确切地说是一种二甲氧基甲苯的合成方法，其合成方法用20mol％(S)α-苯乙胺锌氮、铜氮配合物，(R)α-苯乙胺锌氮、铜氮配合物做催化剂，苯甲醛1mmol，三甲基硅腈3mmol，用2mL无水甲醇做溶剂，室温反应3天后，柱层析分离，用石油醚/二氯甲烷(7/3)洗脱，将收集的第二组分点旋干，得化合物二甲氧基甲苯。
Description
一、技术领域
本发明涉及一种化合物及其制备方法，特别涉及一种缩醛化合物及其制备方法，确切地说是一种二甲氧基甲苯的合成方法。
二、背景技术
二甲氧基甲苯的合成方法相继有许多文献报道【1-7】
(1)Highly recyclable，imidazolium derived ionic liquids of low antimicrobial and antifungaltoxicity：A new strategy for acid catalysis.Myles，Lauren；Gore，Rohitkumar；Spulak，Marcel；Gathergood，Nicholas；Connon，Stephen J.，Green Chemistry(2010)，12(7)，1157-1162.
(2)Preparation and catalytic use of silica-polymer core-shell microspheres withimidazolium-styren e copolymer shells.Yamada，Yu-Dai；Qiao，Kun；Bao，Quan-Xi；
Tomida，Daisuke；Nagao，Daisuke；Konno，Mikio；Yokoyama，Chiaki，Catalysis Communications(2009)，11(4)，227-231.
(3)Single-step conversion of electron-deficient aldehydes into the corresponding esters in aqueousalcohols in the presence of iodine and sodium nitrite.Kiran，Y.B.；Ikeda，Reiko；Sakai，Norio；Konakahara，Takeo，Synthesis(2010)，(2)，276-282.
(4)Pyridinium ion catalysis of carbonyl protection reactions.Procuranti，Barbara；Myles，Lauren；Gathergood，Nicholas；Connon，Stephen J.Synthesis(2009)，(23)，4082-4086.
(5)Unexpected catalysis：aprotic pyridinium ions as active and recyclable Bronsted acid catalystsin protic media.Procuranti，Barbara；Connon，Stephen J，Organic Letters(2008)，10(21)，4935-4938.
(6)Microwave-assisted preparation of 1-butyl-3-methylimidazolium tetrachlorogallate and itscatalytic use in acetal formation under mild conditions.Kim，Yong Jin；Varma，Raj ender S.Tetrahedron Letters(2005)，46(43)，7447-7449.
(7)Photochemical Acetalization of Carbonyl Compounds in Protic Media Using an in SituGenerated Photocatalyst.de Lijser，H.J.Peter；Rangel，Natalie AnnJournal of OrganicChemistry(2004)，69(24)，8315-8322.
申请人用20mol％(S)α-苯乙胺锌氮、铜氮配合物和20mol％(R)α-苯乙胺锌氮、铜氮配合物做催化剂做催化剂不对称催化苯甲醛腈硅化反应过程中，用甲醇作溶剂不仅得到手性目标产物，而且得到了一种二甲氧基甲苯产品。
二、发明内容
本发明旨在提供化合物二甲氧基甲苯。所要解决的技术问题是一步合成得到目标产物。
本合成方法包括合成和分离，所述的合成用20mol％(S)α-苯乙胺锌氮、铜氮配合物，(R)α-苯乙胺锌氮、铜氮配合物做催化剂，2-甲基苯甲醛1mmol，三甲基硅腈3mmol，用2mL无水甲醇做溶剂，室温反应3天后，柱层析分离，用石油醚/二氯甲烷(7/3)洗脱，将收集的第二组分点旋干，得化合物二甲氧基苯。
催化剂的结构如下：
1、(S)α-苯乙胺锌氮、铜氮配合物：
式中ML：1a：Zn(OOCCH3)2
1b：Cu(OOCCH3)2
1c：CuCl2
2、(R)α-苯乙胺锌氮、铜氮配合物：
式中ML：2a：Zn(OOCCH3)2
2b：Cu(OOCCH3)2
2c：CuCl2
配合物(1a、2a)的合成方法以手性(S)/(R)α-苯乙胺与二水合醋酸锌为原料，包括合成、分离、结晶和洗涤，所述的合成是α-苯乙胺与二水合醋酸锌在四氢呋喃溶剂中回流反应22～26小时，分离、除去沉淀后真空脱溶至粘稠状液体，加入石油醚和无水乙醇混合溶剂形成饱和溶液后冷冻结晶，分离，结晶即是目标产物，最后用石油醚洗涤、经元素分析和X-衍射等手段表征、确认。
配合物(1b、2b)的合成方法以(S)/(R)α-苯乙胺与一水合醋酸铜为原料，包括合成、分离、结晶和洗涤，所述的合成是α-苯乙胺与一水合醋酸铜在无水乙醇溶剂中回流反应22～26小时，用正己烷重结晶，经元素分析和X-衍射等手段表征、确认。
配合物(1c、2c)的合成方法以(S)/(R)α-苯乙胺与二水合氯化铜为原料，包括合成、分离、结晶和洗涤，所述的合成是α-苯乙胺与二水合氯化铜在四氢呋喃溶剂中回流反应22～26小时，真空脱溶得到淡蓝色固体，即是目标产物，重结晶纯化后经元素分析和X-衍射等手段表征、确认。
合成反应如下：
本合成方法一步得到目标产物，工艺简单，操作方便。
其反应机理可推测如下：
苯甲醛与三甲基硅腈，在20mol％催化剂做路易斯碱催化剂作用下，苯甲醛与甲醇进行缩合，得到化合物二甲氧基甲苯。
四、附图说明
图1是化合物二甲氧基甲苯的NMR氢谱图。
三、具体实施方式
在25mL烧瓶中，加入2mL无水甲醇，苯甲醛0.1mL(1mmol)，三甲基硅腈3mmol，催化剂I，II及III(0.20mmol)，将反应物在室温下搅拌3天，停止反应，柱层析分离，用石油醚/二氯甲烷(7/3)洗脱，将收集的第二组分点自然旋干得化合物二甲氧基甲苯。其产率均在30％左右。1HNMR(500MHz，CDCl3，27℃)，δ(ppm)＝7.20～7.50(m，1H)，7.11～7.20(m，3H)，5.43(s，1H)，3.3(s，6H)，2.34(s，3H).
手性催化剂I，II及III的合成
1、1a：手性(S)-α-苯乙胺醋酸锌金属有机配合物的合成
称取2.191g Zn(CH3COO)2·2H2O(0.01mol)加入到100mL圆底烧瓶中，再加入25mL四氢呋喃作溶剂，加入搅拌子，在搅拌情况下用针筒量取2.7mL α-苯乙胺(0.02mol)加入到烧瓶中，装上冷凝管，接通自来水，放在磁力加热搅拌器上加热回流反应24h，用旋转蒸发仪除去溶剂，用石油醚重结晶，得无色晶体，产率90％
1HNMR(500MHz，CDCl3)7.22～7.31(m，10H)，4.06～4.07(d，J＝6.5Hz，1H)，3.06(br，1H)，1.94(s，6H)，1.40～1.42(d，J＝6.5Hz，6H).13C NMR(75MHz，CDCl3)179.70，144.04，128.94，127.92，125.92，51.82，23.94，23.10.IR(KBr)cm-1：3130，1620，1390，1170，702。
2、1b：手性(S)-α-苯乙胺醋酸铜金属有机配合物的合成
称取2.000g Cu(CH3COO)2·H2O(0.01mol)加入到100mL圆底烧瓶中，再加入25mL四氢呋喃作溶剂，在搅拌情况下用针筒量取3mL α-苯乙胺(mol，稍过量点)加入到烧瓶中，反应完成后，在旋转蒸发仪上抽干后为粘稠状液体，用正己烷重结晶，得淡蓝色晶体，产率＝80.1％，[a]25 D＝+14.15°(c 0.4776，THF)Elemental analysis：found：N：6.45％，C：56.17％，H：6.56％；Calculate：N：6.61％，C：56.65％，H：6.62％.
3、1c：手性(S)-α-苯乙胺氯化铜金属有机配合物的合成
称取1.7052g CuCl2·2H2O(0.01mol)，放入100mL的圆底烧瓶中，向烧瓶中加入25mL的无水乙醇溶液，然后，用注射器向上述溶液中，加入3.0ml(23.2mmol)的α-苯乙胺(0.02mol)，在磁力搅拌器上加热回流，反应24小时，得到黄绿色的液体，于室温下静止，挥发，几天后有淡蓝色的针状晶体析出，产率＝51.6％.[a]25 D＝-164.8°(c 0.0364，THF)，IR(KBr)cm-1：3319，3232，3149，2975，2928，1593，1580，1496，1452，1388.，1375，1228，1163，1195，1134，1077，1027，1002，988，892，775，760.HRMS(EI)：m/z(％)：Anal calcd for C16H22N2Cl2Cu：375.0456；found：375.0458，Elemental analysis：found：N：7.23％；C：50.78％，H：5.98％；Calculate：N：7.43％，C：50.58％，H：5.88％.
4、2a：手性(R)-α-苯乙胺醋酸锌金属有机配合物的合成
反应步骤同1相同。
[a]25 D＝+26.70°(c 0.1872，THF)，产率：86.8％，Elemental analysis：found：N：6.45％，C：56.17％，H：6.56％；Calculate：N：6.61％，C：56.63％，H：6.62％.
analysis：found：N：6.45％，C：56.17％，H：6.56％；Calculate：N：6.61％，C：56.63％，H：6.62％.
5、2b：手性(R)-α-苯乙胺醋酸铜金属有机配合物的合成
反应步骤同2相同
[a]25 D＝+14.15°(c 0.4776，THF)，产率：80.1％，Elemental analysis：found：N：6.45％，C：56.17％，H：6.56％；Calculate：N：6.61％，C：56.65％，H：6.62％.
6、2c：手性(R)-α-苯乙胺氯化铜金属有机配合物的合成
反应步骤同3相同，[a]25 D＝+81.78°(c 0.0428，THF)，产率：53.4％，Elemental analysis：found：N：7.13％；C：50.99％，H：5.96％；Calculate：N：7.43％，C：50.58％，H：5.88％.
Claims (1)
1.一种二甲氧基甲苯的合成方法，包括合成和分离，其特征在于所述的合成用20mol％(S)-α-苯乙胺锌氮、铜氮配合物，(R)-α-苯乙胺锌氮、铜氮配合物做催化剂，苯甲醛1mmol，三甲基硅腈3mmol，用2mL无水甲醇做溶剂，室温反应3天后，柱层析分离，用7/3的石油醚/二氯甲烷洗脱，将收集的第二组分点旋干，得化合物二甲氧基甲苯，
其中，(S)-α-苯乙胺锌氮配合物为
(S)-α-苯乙胺铜氮配合物为
(R)-α-苯乙胺锌氮配合物为
(R)-α-苯乙胺铜氮配合物为
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| F. Gandara et al..A new scandium metal organic framework built up from octadecasil zeolitic cages as heterogeneous catalyst.《Chem. Commun.》.2009,2393-2395. |
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