曙红催化的缩醛化反应研究
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摘要
以醇溶性曙红为催化剂,在温和条件下高效催化缩醛化反应,该催化体系适应于不同种类的脂肪醛或芳香醛与短链一元醇或二元醇的羰醇缩合反应,于室温反应24 h,缩醛化产物收率58%~99%,其结构经~1H NMR,~(13)C NMR和HR-MS确证。
The acetalization reaction of different kinds of aliphatic aldehydes or aromatic aldehydes with short chain monohydric alcohols and diols was achieved under mild conditions catalyzed by the alcohol-soluble Eosin Y.The yield of acetal compounds were 58%~99% after reaction for 24 h at room temperature.The structures were confirmed by ~1 H NMR,~(13) C NMR and HR-MS.
The acetalization reaction of different kinds of aliphatic aldehydes or aromatic aldehydes with short chain monohydric alcohols and diols was achieved under mild conditions catalyzed by the alcohol-soluble Eosin Y.The yield of acetal compounds were 58%~99% after reaction for 24 h at room temperature.The structures were confirmed by ~1 H NMR,~(13) C NMR and HR-MS.
引文
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[2]Iwamoto M,Tanaka Y,Sawamura N,et al.Remarkable effect of pore size on the catalytic activity of mesoporous silica for the acetalization of cyclohexanone with methanol[J].J Am Chem Soc,2003,125:13032.
[3]Leonard N M,Oswald M C,Freiberg D A,et al.A simple and versatile method for the synthesis of acetals from aldehydes and ketones using bismuth triflate[J].J Org Chem,2002,67:5202-5207.
[4]Smitha G,Reddy C S.A facile and efficient Zr Cl4catalyzed conversion of aldehydes to geminal-diacetates and dipivalates and their cleavage[J].Tetrahedron,2003,59:9571-9576.
[5]Jia L Q,Jiang H F,Li J H.Palladium(II)-catalyzed oxidation of acrylate esters to acetals in supercritical carbon dioxide[J].Chem Commun,1999,985-986.
[6]Nieendick Claus,Schmid Karl Heinz.Aqueous perlescent concentrate for cosmelics:EP 1060740[P].2000.
[7]Torok D S,Fifueroa J J,Scott W J.1,3-Dioxolane formation via Lewis acid-catalyzed reaction of ketones with oxiranes[J].J Org Chem,1993,58:7274-7276.
[8]Kamble V T,Bandgar B P,Muley D B,et al.An expedient and efficient cemoselective protection of carbonyl compounds and transthioacetalization of O,Oand S,O-acetals catalyzed by HBF4-Si O2[J].Journal of Molecular Catalysis A:Chemical,2007,268:70-75.
[9]Smith B M,Kubczyk T M,Graham A E.Indium(III)triflate catalysed transacetalisation reactions of diols and triols under solvent-free conditions[J].Tetrahedron,2012,68:7775-7781.
[10]Fang D,Gong K,Shi Q R,et al.A green procedure for the protection of carbonyls catalyzed by novel taskspecific room-temperature ionic liquid[J].Catalysis Communications,2007,8:1463-1466.
[11]Procuranti B,Connon S J.Unexpected catalysis:Aprotic pyridinium ions as active and recyclable Brnsted acid catalysts in protic media[J].Org Lett,2008,21:4935-4938.
[12]Myles L,Gore R G,Gathergood N,et al.The catalytic versatility of low toxicity dialkyltriazolium salts:In situ modification facilitates diametrically opposed catalysis modes in one pot[J].Chem Commun,2013,49:5316-5318.
[13]Lijser H J P D,Rangel N A.Photochemical acetalization of carbonyl compounds in protic media using an in situ generated photocatalyst[J].J Org Chem,2004,69:8315-8322.