A fast and efficient deprotection of aldehydes from acylals using a Wells-Dawson heteropolyacid catalyst (H6P2W18O62 • 24H2O)

被引:16
|
作者
Romanelli, GP
Autino, JC
Baronetti, G
Thomas, HJ
机构
[1] Univ Nacl La Plata, Fac Ciencias Exactas, Dept Quim, Lab Estudio Compuestos Organ, La Plata, Argentina
[2] Univ Nacl La Plata, Fac Ciencias Exactas, CINDECA, La Plata, Argentina
[3] Univ Buenos Aires, Fac Ingn, Dept Ingn Quim, RA-1053 Buenos Aires, DF, Argentina
关键词
acylal; aldehyde; 1,1-diacetate; heteropolyacid; protecting group; Wells-Dawson catalyst;
D O I
10.1081/SCC-200034783
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rapid and efficient method for the deprotection of aldehyde l,l-diacetates is described. The reaction was carried out using a Wells-Dawson type catalyst supported on silica. The catalyst, used in 1% molar quantity, is easily recoverable and reusable and maintains the activity after its use in four consecutive reaction batches. The yield of the deprotection was 92-100% (15 examples including nitrobenzaldehyde l, l-diacetates). Reaction conditions involve short times and the use of toluene as the solvent; isolation is simple and the products are nearly pure.
引用
收藏
页码:3909 / 3914
页数:6
相关论文
共 50 条
  • [1] A simple and efficient solvent-free preparation of acetone diperoxide using a Wells-Dawson heteropolyacid (H6P2W18O62•24H2O) as the catalyst
    Romanelli, Gustavo P.
    Sathicq, Angel G.
    Autino, Juan C.
    Thomas, Horacio J.
    Baronetti, Graciela T.
    [J]. AFINIDAD, 2007, 64 (530) : 535 - 537
  • [2] Reduced Silver Salt of Wells-Dawson Heteropolyacid H6P2W18O62 as a Bi-Functional Catalyst
    Tomasz Kasza
    Adam Bielański
    [J]. Catalysis Letters, 2009, 128 : 307 - 312
  • [3] Reduced Silver Salt of Wells-Dawson Heteropolyacid H6P2W18O62 as a Bi-Functional Catalyst
    Kasza, Tomasz
    Bielanski, Adam
    [J]. CATALYSIS LETTERS, 2009, 128 (3-4) : 307 - 312
  • [4] Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a Wells-Dawson acid (H6P2W18O62•24H2O)
    Romanelli, GP
    Thomas, HJ
    Baronetti, GT
    Autino, JC
    [J]. TETRAHEDRON LETTERS, 2003, 44 (06) : 1301 - 1303
  • [5] TiO2 and SiO2 supported Wells-Dawson heteropolyacid H6P2W18O62 as the catalyst for ETBE formation
    Pozniczek, J
    Lubanska, A
    Micek-Ilnicka, A
    Mucha, D
    Lalik, E
    Bielanski, A
    [J]. APPLIED CATALYSIS A-GENERAL, 2006, 298 : 217 - 224
  • [6] An efficient and green synthetic protocol for the preparation of bis(indolyl)methanes catalyzed by H6P2W18O62•24H2O, with emphasis on the catalytic proficiency of Wells-Dawson versus Keggin heteropolyacids
    Tayebee, Reza
    Nehzat, Farzaneh
    Rezaei-Seresht, Esmail
    Mohammadi, Farokhzad Z.
    Rafiee, Ezzat
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2011, 351 : 154 - 164
  • [7] A METHODOLOGY STUDY OF HYDROPHOSPHONYLATION OF ALDEHYDES DERIVATIVES WITH H6P2W18O62•14H2O AS A CATALYST
    Aouf, Zineb
    Boughaba, Sara
    Lakrout, Salah
    Bechiri, Ouahiba
    Aouf, Nour-Eddine
    [J]. CHEMISTRY & CHEMICAL TECHNOLOGY, 2020, 14 (02): : 154 - 160
  • [8] P2W18O62•24H2O as an efficient and recyclable catalyst for the ecofriendly preparation of β-aminocrotonates
    Sanchez, Laura M.
    Sathicq, Angel G.
    Baronetti, Graciela T.
    Thomas, Horacio J.
    Romanelli, Gustavo P.
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2013, 91 (02): : 137 - 142
  • [9] Performance of NOx capture with Dawson polyoxometalate H6P2W18O62•28H2O
    Zhang, Xveyoung
    Wang, Rui
    Zhu, Hongjian
    Chen, Yongliang
    [J]. CHEMICAL ENGINEERING JOURNAL, 2020, 400
  • [10] H6P2W18O62•14H2O as an efficient catalyst for the green synthesis of α-aminophosphonates from α-amino acids
    Boughaba, Sara
    Aouf, Zineb
    Bechiri, Ouahiba
    Mathe-Allainmat, Monique
    Lebreton, Jacques
    Aouf, Nour-Eddine
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2020, 196 (01) : 28 - 35