| 6-(3-甲基-4-对甲苯磺酰基-2-丁烯基)-2,3,4,5-四甲氧基甲苯的合成 |
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| 引用本文： | 黎其万,王继良. 6-(3-甲基-4-对甲苯磺酰基-2-丁烯基)-2,3,4,5-四甲氧基甲苯的合成[J]. 精细化工, 2003, 20(11): 668-670 |
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| 作者姓名： | 黎其万 王继良 |
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| 作者单位： | 1. 云南省农业科学院,生物技术研究所,云南,昆明,650223
2. 昆明医学院,药学系,云南,昆明,650031 |
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| 基金项目： | 云南省农业生物技术重点实验室开放基金项目(2000G02) |
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| 摘 要： | 对甲酚(Ⅰ)在铁粉催化下与溴反应得到2,3,6 三溴 4 甲基苯酚(Ⅱ)(收率78%);Ⅱ在碘化亚铜催化下与甲醇钠反应后再与硫酸二甲酯反应得到2,3,4,5 四甲氧基甲苯(Ⅲ)(收率92 5%);Ⅲ与溴反应得到6 溴 2,3,4,5 四甲氧基甲苯(Ⅳ)(收率85%);Ⅳ与镁反应得到格氏试剂后,在碘化亚铜催化下与(E) 4 氯 2 甲基 1 对甲苯磺酰基 2 丁烯(Ⅴ)偶联反应合成了辅酶Q10中间体6 (3 甲基 4 对甲苯磺酰基 2 丁烯基) 2,3,4,5 四甲氧基甲苯(Ⅵ)(收率81%)。四步反应总收率49 6%,产物经1HNMR确证其双键为E 异构体。
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| 关 键 词： | 6-(3-甲基-4-对甲苯磺酰基-2-丁烯基)-2,3,4,5-四甲氧基甲苯 辅酶Q10中间体 2,3,4,5-四甲氧基甲苯 对甲酚 |
| 文章编号： | 1003-5214(2003)11-0668-03 |
Synthesis of 6-(3-Methyl-4-p-toluenesufonyl-2-butenyl)- 2,3,4,5-tetramethoxytoluene |
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| LI Qi-wan,WANG Ji-liang. Synthesis of 6-(3-Methyl-4-p-toluenesufonyl-2-butenyl)- 2,3,4,5-tetramethoxytoluene[J]. Fine Chemicals, 2003, 20(11): 668-670 |
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| Authors: | LI Qi-wan WANG Ji-liang |
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| Affiliation: | LI Qi-wan~1,WANG Ji-liang~2 |
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| Abstract: | 6-(3-methyl-4-p-toluenesufonyl-2-butenyl)-2,3,4,5-tetramethoxytoluene(Ⅵ),an intermediate of coenzyme Q10,was synthesized from p-cresol(Ⅰ) via four step procedure in overall yield of 49.6%.Bromination of Ⅰ in the presence of Fe powder gave 2,3,6-tribromo-4-methyphenol (Ⅱ) in 78% yield.Ⅱ reacted with CH3ONa in the presence of CuI,and then with (CH3)2SO4 to give 2,3,4,5-tetramethoxytoluene (Ⅲ) in 92.5% yield.Compound Ⅲ was brominated to give 6-bromo-2,3,4,5-tetramethoxytoluene (Ⅳ) in 85% yield,Ⅳ reacted with Mg,followed by reaction with (E)-4-cholro-2-methyl-p-toluenesufonyl-2-butene (Ⅴ),to give compound Ⅵ in 81% yield.The double bond of compound Ⅵ was confirmed to be E-isomer by 1HNMR. |
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| Keywords: | 6-(3-methyl-4-p-toluenesufonyl-2-butenyl)-2 3 4 5-tetramethoxytoluene intermediate of coenzyme Q_(10_ 2 3 4 5-tetramethoxytoluene p-cresol |
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