流体化学在对羟基苯乙酮合成中的应用
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摘要
以苯酚为原料,采用流体化学技术,依次经醋酐酯化和酸催化Fries重排反应合成了对羟基苯乙酮,其结构经~1H NMR,~(13)C NMR和MS(ESI)确证。使用流体化学反应技术合成对羟基苯乙酮具有操作简便、反应选择性好和产品收率高等优点。
p-Hydroxyacetophenone was synthesized using phenol as the raw material through esterification and Fries rearrangement under acid condition. Both steps were carried out under continuous flow conditions. The structure was confirmed by ~1H NMR, ~(13)C NMR and MS(ESI). Synthesizing p-hydroxyacetophenone via flow chemistry has several advantages such as simple operation, good selectivity, high yield, etc.
p-Hydroxyacetophenone was synthesized using phenol as the raw material through esterification and Fries rearrangement under acid condition. Both steps were carried out under continuous flow conditions. The structure was confirmed by ~1H NMR, ~(13)C NMR and MS(ESI). Synthesizing p-hydroxyacetophenone via flow chemistry has several advantages such as simple operation, good selectivity, high yield, etc.
引文
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[2] 庄媛,刘杰民,姚喆.化学实验与科研方法课程教学模式探讨[J].大学化学,2017,32(7):44-47.
[3] 鲍继明,戴淑昌.对羟基苯乙酮的合成[J].合成化学,2002,10(3):281-282.
[4] PLUTSCHACK M B,PIEBER B,GILMORE K.et al.The hitchhiker’s guide to flow chemistry II[J].Chem Rev,2017,117(18):11796-11893.
[5] PORTA R,BENAGLIA M,PUGLISI A,et al.Flow chemistry:Recent developments in the synthesis of pharmaceutical products[J].Org Process Res Dev,2016,20(1):2-25.
[6] MOVSISYAN M,DELBEKE E,BERTON J,et al.Taming hazardous chemistry by continuous flow technology[J].Chem Soc Rev,2016,45:4892-4928.
[7] MURASHIGE R,HAYASHI Y,OHMORI S,et al.Comparisons of O-acylation and Friedel-Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid:Effective synthesis of optically active homotyrosines[J].Tetrahedron,2011,67(3):641-649.
[8] 马建标,嵇耀武,陈恒昌.三氟化硼催化的苯酚Friedel-Craft酰化反应[J].化学试剂,1991,13(3):152,191.
[9] PRAKASH G,PANJA C,MATHEW T,et al.BF3-H2O catalyzed Fries rearrangement of phenolic esters[J].Catalysis Lett,2007,114(1-2):24-29.
[10] COMMARIEU A,HOELDERICH W,LAFFITTE J,et al.Fries rearrangement in methane sulfonic acid,an environmentally friendly acid[J].J Mol Catal A Chem,2002,(182-183):137-141.