CN1210564A - 2-苯并[c]呋喃酮类化合物的制备方法 - Google Patents
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Abstract
本发明提供了通过阴极还原邻苯二甲酸或其中羧基可被通过缩合反应而衍生自羧基的单元置换、而且邻苯二甲酸的邻亚苯基单元中的一个或多个氢可被惰性基团置换的邻苯二甲酸衍生物制备2-苯并[c]呋喃酮类化合物的方法,该方法包括在单一的电解池中于含有少于50%wt.水的有机溶剂中进行所述还原。
Description
本发明涉及通过阴极还原邻苯二甲酸衍生物制备2-苯并[c]呋喃酮类化合物的新方法。
2-苯并[c]呋喃酮类化合物为合成作物保护剂特别需要的中间体。
DE-A-2 144 419中公开了制备2-苯并[c]呋喃酮类化合物的电化学方法,该方法包括在高至65℃的温度下,在含有多至50%有机溶剂的水溶液中,在其氢超电势大于Cu的金属(例如铅)上阴极还原邻苯二甲酸铵。在这些条件下,如果还原在分离电解池中进行,则能够以令人满意的收率实现2-苯并[c]呋喃酮类化合物的制备。
DE-A-2 510 920中描述了特别纯净的2-苯并[c]呋喃酮类化合物的制备。这一文献教导了可在高至100℃的温度下,在氢超电势大于Cu的金属上阴极还原邻苯二甲酸或邻苯二甲酸酐的充氨水溶液。此方法也需要使用分离电解池。2-苯并[c]呋喃酮类化合物的分离按下所述进行:在35-100℃下酸化电解混合物,如果需要,酸化可以在除去过量氨之后进行,分离出2-苯并[c]呋喃酮类化合物沉淀。
但是,由于上述方法需要使用分离电解池,因而在这些方法中需要2套电解池电路,这样这些方法就需要投入过多资金用于与电解池有关的设备。此外,采用2套电解池电路工作还具有下列缺点:
电解池电路必须用膜或隔膜分开;这样因存在热阻而导致能量损失。为将这种损失降至最低,通常在至少一个室中装有支持电解质水溶液(>80%H2O)。在阴极还原方法中,这种水溶液为阳极电解液,这样大大减少了开发阳极反应的有效选择方案。而且通常所形成的阳极产物仅为氢。
另外,迄今为止的已知方法都可能发生阳极腐蚀和阴极中毒的危险性。
本发明的目的是提供一种技术简单的并能以高纯度和高收率制备2-苯并[c]呋喃酮类化合物的方法,该方法无现有技术中所述的那些缺点,更特别的是该方法开辟了开发阳极反应制备非氢产物的可能性。
我们现已发现,本发明的这一目的可通过阴极还原邻苯二甲酸或其中羧基可被通过缩合反应而衍生自羧基的单元置换、而且邻苯二甲酸的邻亚苯基单元中的一个或多个氢可被惰性基团置换的邻苯二甲酸衍生物制备2-苯并[c]呋喃酮类化合物的方法实现,该方法包括在单一(ungeteilte)电解池中于含有低于50%wt.水的有机溶剂中进行上述还原。
制备2-苯并[c]呋喃酮类化合物所用的起始物质尤其为通式Ⅰ化合物:其中各取代基的定义如下:R1,R2,R3和R4彼此独立地为氢,C1-C4-烷基或卤素,R5,R6:a)彼此独立地为-COOH或COOX,其中X为C1-C4-烷基,
b)取代基R5或R6之一为-COONY4,而另一个为CONH2,其
中Y为C1-C4-烷基或氢,
c)R5和R6一起表示-CO-O-CO-。
特别优选其中R1,R2,R3和R4各自为氢的邻苯二甲酸衍生物,其中特别是邻苯二甲酸二(C1-C3-烷基)酯,尤指邻苯二甲酸二甲酯。
对于其中R5和R6的定义同b)的式Ⅰ化合物,特别优选铵盐形式,尤其是邻氨甲酰苯甲酸的铵盐。
适宜的(阴极和阳极)电极材料主要是市场上可购得的石墨及碳电极。
电解液通常为2至40%(重量)邻苯二甲酸或邻苯二甲酸衍生物在有机溶剂中的溶液,其中所述有机溶剂中优选含有低于25%,特别优选低于5%wt.水。
适用的有机溶剂尤为脂族C1-C4醇,特别是甲醇或乙醇,或为所述醇与羧酰胺如二甲基甲酰胺或叔丁基甲酰胺的混合物。
电解液中所包含的适宜支持电解质(Leitsalze)一般为烷基硫酸盐,例如甲基硫酸盐,或季铵盐,特别是卤化或四氟硼酸-四(C1-C4-烷基)铵,其用量通常占电解液重量的0.4-10%。
对于阳极共生产方法(anodic coproduction process),适宜使用这样常规有机化合物作为阳极去极化剂,它们适于电化学氧化的性能对本领域技术人员而言是公知的。一些阳极共生产方法优选在有介体存在下进行。例如,可能的阳极共生产方法及其介体化见D.Kyriakou在《现代有机电化学》(Modern Electroorganic Chemistry)[Springer,Berlin 1994],第4.2.章节中所述。
特别适用的阳极共生产方法是氧化C-O或C-N单或双键,例如氧化羧酸、芳基甲烷、醛、酰胺、醇和杂环,或特别是萘或活化的CH基的氧化的C-C连接。
适用的介体尤为卤素化合物,特别是溴化物或碘化物。
其它方法参数如温度和电流密度并不重要,只要求它们保持在有机化合物的电化学反应的常规范围之内。有关它们的进一步说明例如参见DE-A-2 510 920。
电解液混合物的后处理方式主要取决于阳极共产物的性质,并且可采用通常公知的分离方法如蒸馏,沉淀或重结晶来进行。一种从许多不溶于碱性含水介质的有机副产物分离出大多数2-苯并[c]呋喃酮类化合物的特别容易的方法包括将2-苯并[c]呋喃酮化合物溶于充氨水溶液中,分离水相,然后酸化水相再沉淀2-苯并[c]呋喃酮化合物(同样可参见DE-A-2 510920)。
本发明方法以一种技术简单的方式高收率和高纯度地得到2-苯并[c]呋喃酮化合物。同时,通过阳极氧化反应能够共生制得各种有价值产物,而且不会降低阴极的电流效率和物料收率。
实施例1仅生产有价值产物2-苯并[c]呋喃酮
将含500g邻苯二甲酸二甲酯(2.56mol),1600g叔丁基甲酰胺和375g甲醇以及25g四丁基四氟硼酸铵的溶液加入到电解池中,该电解池配置有10块双极接通的环形石墨圆盘(每侧表面:147dm2),电极间距离为0.7mm。在60℃下用2.5A电流强度电解11.5小时。
蒸除溶剂混合物之后,在10mbar压力下减压蒸馏,得到2.18mol 2-苯并[c]呋喃酮,即收率为85%。
回收未分解的叔丁基甲酰胺,阳极过程为氧化甲醇,主要得到甲酸甲酯产物。实施例2共生产2-苯并[c]呋喃酮和N-甲氧基甲基-N-甲基甲酰胺
在实施例1所用的电解池中,放入2.56mol邻苯二甲酸二甲酯,750g甲醇,1225g二甲基甲酰胺(DMF)和25g甲基硫酸三乙基甲铵,并在5A和50℃下电解6.9h。除形成2.1mol 2-苯并[c]呋喃酮(物料收率;82%)外,还形成4.1mol(电流效率:64%)N-甲氧基甲基-N-甲基甲酰胺。实施例3-9
按照和实施例2类似的方式,在每一实施例中,采用表1中所述的相应起始物料制备2-苯并[c]呋喃酮和各种阳极共产物。表1
1)%wt.基于甲醇
实施例 | 共溶剂1) | 支持电解质 | 阳极去极化剂 | 2-苯并[c]呋喃酮的收率 | 阳极产物 |
3 | H2O(3%) | 碘化四丁铵 | 环己酮 | 80% | 2,2′-二甲氧基环己醇 |
4 | 溴化四乙铵 | 呋喃 | 92% | 2,5-二甲氧基二氢呋喃 | |
5 | DMF(2%) | 四氟硼酸四丁铵 | 对-二甲苯 | 85% | 甲苯甲醛缩二甲醇 |
6 | DMF(20%) | 四氟硼酸四丁铵 | 叔丁基甲苯 | 90% | 叔丁基苯甲醛缩二甲醇 |
7 | 二甲氧基甲烷 | 溴化四乙铵 | 甲醇 | 89% | 主要为甲酸甲酯 |
8 | DMF(1%) | 溴化四乙铵 | 甲醇 | 85% | 主要为甲酸甲酯 |
9 | 水(10%) | 溴化四乙铵 | 羟基新戊醛 | 84% | 羟基新戊酸甲酯 |
Claims (9)
1.阴极还原邻苯二甲酸或其中羧基可被通过缩合反应而衍生自羧基的单元置换、而且邻苯二甲酸的邻亚苯基单元中的一个或多个氢可被惰性基团置换的邻苯二甲酸衍生物制备2-苯并[c]呋喃酮类化合物的方法,其特征在于在单一的电解池中于含有低于50%wt.水的有机溶剂中进行所述还原。
3.如权利要求1或2的方法,其中所用的邻苯二甲酸衍生物为邻苯二甲酸二(C1-C3烷基)酯。
4.如权利要求1-3中任一项的方法,其中使用石墨或碳电极。
5.如权利要求1-4中任一项的方法,其中所用的有机溶剂为脂族C1-C4醇或这种醇与羧酰胺的混合物。
6.如权利要求1-5中任一项的方法,其中所用的支持电解质为季铵盐。
7.如权利要求1-6中任一项的方法,其中用于阳极共生产方法的阳极去极化剂为适于电化学氧化的常规有机化合物。
8.如权利要求1-7中任一项的方法,其中用于阳极共生产方法的介体为卤素化合物。
9.如权利要求8的方法,其中所用介体为溴化物或碘化物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19618854.7 | 1996-05-10 | ||
DE19618854A DE19618854A1 (de) | 1996-05-10 | 1996-05-10 | Verfahren zur Herstellung von Phthaliden |
Publications (2)
Publication Number | Publication Date |
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CN1210564A true CN1210564A (zh) | 1999-03-10 |
CN1058302C CN1058302C (zh) | 2000-11-08 |
Family
ID=7793943
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN97192040A Expired - Fee Related CN1058302C (zh) | 1996-05-10 | 1997-04-28 | 2-苯并[c]呋喃酮类化合物的制备方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US6063256A (zh) |
EP (1) | EP0902846B1 (zh) |
JP (1) | JP3946260B2 (zh) |
CN (1) | CN1058302C (zh) |
CA (1) | CA2254788C (zh) |
DE (2) | DE19618854A1 (zh) |
ES (1) | ES2150770T3 (zh) |
WO (1) | WO1997043464A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100402515C (zh) * | 2000-06-28 | 2008-07-16 | 中国医学科学院药物研究所 | 用作抗惊厥药的取代2-苯并[c]呋喃酮 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR018507A1 (es) * | 1997-09-19 | 2001-11-28 | Basf Se | Proceso de recuperacion de un compuesto derivado del acido ftalico de una mezcla de reaccion en la que se sintetiza este compuesto |
DE19741423A1 (de) * | 1997-09-19 | 1999-03-25 | Basf Ag | Verfahren zur Herstellung von Phthaliden |
DE19808296A1 (de) * | 1998-02-27 | 1999-09-02 | Basf Ag | Verfahren zur selektiven Hydrolyse von Acetalen bzw. Ketalen in Gegenwart von Phthaliden |
DE19944989A1 (de) | 1999-09-20 | 2001-03-22 | Basf Ag | Verfahren zur elektrolytischen Umwandlung von Furanderivaten |
DE19944990A1 (de) | 1999-09-20 | 2001-03-22 | Basf Ag | Verfahren zur elektrolytischen Umwandlung von organischen Verbindungen |
DE10057888A1 (de) | 2000-11-22 | 2002-05-23 | Basf Ag | Herstellung von Butantetracarbonsäurederivaten mittels gekoppelter Elektrosynthese |
DE10058304A1 (de) * | 2000-11-24 | 2002-05-29 | Basf Ag | Verfahren zur Herstellung von alkoxylierten Carbonylverbindungen durch ein anodisches Oxidationsverfahren unter Nutzung der kathodischen Koppelreaktion zur organischen Synthese |
JP2015527483A (ja) * | 2012-06-15 | 2015-09-17 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 求核試薬の存在下での有機基材の陽極酸化 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2510920A1 (de) * | 1975-03-13 | 1976-09-30 | Basf Ag | Verfahren zur elektrochemischen herstellung von phthalid |
DE2630927A1 (de) * | 1976-07-09 | 1978-01-19 | Basf Ag | Verfahren zur herstellung von phthalidcarbonsaeure-(5) |
-
1996
- 1996-05-10 DE DE19618854A patent/DE19618854A1/de not_active Withdrawn
-
1997
- 1997-04-28 JP JP54044397A patent/JP3946260B2/ja not_active Expired - Fee Related
- 1997-04-28 ES ES97921810T patent/ES2150770T3/es not_active Expired - Lifetime
- 1997-04-28 WO PCT/EP1997/002185 patent/WO1997043464A1/de active IP Right Grant
- 1997-04-28 US US09/125,019 patent/US6063256A/en not_active Expired - Fee Related
- 1997-04-28 DE DE59702087T patent/DE59702087D1/de not_active Expired - Fee Related
- 1997-04-28 CN CN97192040A patent/CN1058302C/zh not_active Expired - Fee Related
- 1997-04-28 CA CA002254788A patent/CA2254788C/en not_active Expired - Fee Related
- 1997-04-28 EP EP97921810A patent/EP0902846B1/de not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100402515C (zh) * | 2000-06-28 | 2008-07-16 | 中国医学科学院药物研究所 | 用作抗惊厥药的取代2-苯并[c]呋喃酮 |
Also Published As
Publication number | Publication date |
---|---|
JP3946260B2 (ja) | 2007-07-18 |
DE19618854A1 (de) | 1997-11-13 |
EP0902846A1 (de) | 1999-03-24 |
CN1058302C (zh) | 2000-11-08 |
WO1997043464A1 (de) | 1997-11-20 |
CA2254788C (en) | 2005-03-01 |
ES2150770T3 (es) | 2000-12-01 |
EP0902846B1 (de) | 2000-07-26 |
CA2254788A1 (en) | 1997-11-20 |
DE59702087D1 (de) | 2000-08-31 |
US6063256A (en) | 2000-05-16 |
JP2000511592A (ja) | 2000-09-05 |
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