Facile synthesis of α-hydroxy-α-methyl carboxylic acids by electrochemical carboxylation of methyl aryl ketones

被引：0
|
作者：
Damodar, J
Mohan, SRK
Reddy, SRJ [1 ]
机构：
[1] Sri Venkateswara Univ, Dept Chem, Elect Res Labs, Tirupati 517502, Andhra Pradesh, India
[2] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland
来源：
SYNTHESIS-STUTTGART | 2002年 / 03期
关键词：
carbon dioxide; electrochemical carboxylation; alpha-hydroxy-alpha-methylcarboxylic acids; methyl aryl ketones; sacrificial anode; cyclic voltammetry;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Electrochemical carboxylation of methyl aryl ketones in the presence of atmospheric pressure of carbon dioxide using platinum cathode and dissolved magnesium anode at constant current density of 10 mA/cm(2) gave the corresponding alpha-hydroxy-alpha-methyl carboxylic acids in 79-84% isolated yields. The precursor of cicloprofen, alpha-hydroxy-alpha-methylfluorene-2-acetic acid (1a) and biprofen, alpha-hydroxy-alpha-methybiphenyl-4-acetic acid (2a) were readily obtained in good yield by a similar electrochemical carboxylation of 2-acetylfluorene (1) and 4-acetylbiphenyl (2). Cyclic voltammetric studies showed that the reaction is reversible indicating the preferential generation of stable anion radicals from methyl aryl ketones and that further addition of carbon dioxide does not take place in these electrochemical carboxylations.
引用
收藏
页码：399 / 402
页数：4
相关论文
共 50 条
  • [1] Facile synthesis of α-hydroxy-α-methyl carboxylic acids by electrochemical carboxylation of methyl aryl ketones
    Electrochemical Res. Laboratories, Department of Chemistry, Sri Venkateswara University, Tirupati 517502, India
    Synthesis, 2002, (03) : 399 - 402
  • [2] Electrochemical carboxylation of aliphatic ketones:: Synthesis of β-keto carboxylic acids
    Senboku, Hisanori
    Yamauchi, Yusuke
    Fukuhara, Tsuyoshi
    Hara, Shoji
    ELECTROCHEMISTRY, 2006, 74 (08) : 612 - 614
  • [3] Electrochemical Synthesis of β-Ketonitriles from Aryl Methyl Ketones
    Yavari, Issa
    Shaabanzadeh, Sina
    Sheikhi, Sara
    CHEMISTRYSELECT, 2020, 5 (02): : 564 - 568
  • [4] Trifluoroacetic Anhydride as an Activator in the Acylation of Aryl Methyl Ketones with Carboxylic Acids
    E. A. Shokova
    V. A. Tafeenko
    V. V. Kovalev
    Russian Journal of Organic Chemistry, 2020, 56 : 1770 - 1774
  • [5] Trifluoroacetic Anhydride as an Activator in the Acylation of Aryl Methyl Ketones with Carboxylic Acids
    Shokova, E. A.
    Tafeenko, V. A.
    Kovalev, V. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (10) : 1770 - 1774
  • [6] Electrochemical Carboxylation of Flavones: Facile Synthesis of Flavanone-2-carboxylic Acids
    Senboku, Hisanori
    Yamauchi, Yusuke
    Kobayashi, Natsuko
    Fukui, Akihiro
    Hara, Shoji
    ELECTROCHEMISTRY, 2011, 79 (11) : 862 - 864
  • [7] Stereoselective synthesis of chiral γ-hydroxy-β-methyl methylcarbinols
    Chakraborty, TK
    Thippeswamy, D
    Jayaprakash, S
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1998, 75 (10-12) : 741 - 745
  • [8] Concise enantio- and diastereoselective synthesis of α-hydroxy-α-methyl-β-amino acids
    Roers, R
    Verdine, GL
    TETRAHEDRON LETTERS, 2001, 42 (21) : 3563 - 3565
  • [9] Carboxylic acids from methyl aryl ketones by means of a new composite aerobic oxidation process
    Bjorsvik, HR
    Liguori, L
    González, RR
    Merinero, JAV
    TETRAHEDRON LETTERS, 2002, 43 (28) : 4985 - 4987
  • [10] A FACILE SYNTHESIS OF PHENYLACETIC ACIDS FROM ARYL KETONES
    BELLETIRE, JL
    HOWARD, H
    DONAHUE, K
    SYNTHETIC COMMUNICATIONS, 1982, 12 (10) : 763 - 770
12345