A novel method for the nitration of simple aromatic compounds

被引:130
作者
Smith, K [1 ]
Musson, A
DeBoos, GA
机构
[1] Univ Wales, Dept Chem, Swansea SA2 8PP, W Glam, Wales
[2] ZENECA Huddersfield Works, Huddersfield HD2 1FF, W Yorkshire, England
关键词
D O I
10.1021/jo981557o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Simple aromatic compounds such as benzene, alkylbenzenes, halogenobenzenes, and some disubstituted benzenes are nitrated in excellent yields with high regioselectivity under mild conditions using zeolite beta as a catalyst and a stoichiometric quantity of nitric acid and acetic anhydride. The zeolite can be recycled, and the only byproduct is acetic acid, which can be separated easily from the nitration product by distillation; the process is inexpensive and represents an attractive method for the clean synthesis of a range of nitroaromatic compounds. For example, nitration of toluene gives a quantitative yield of mononitrotoluenes, of which 79% is 4-nitrotoluene; fluorobenzene gives a quantitative yield of mononitro compounds, of which 94% is 4-nitrofluorobenzene; and 2-fluorotoluene gives a 96% yield of mononitro products, of which 90% is the 5-nitro isomer and 10% is the 4-nitro isomer.
引用
收藏
页码:8448 / 8454
页数:7
相关论文
共 34 条
  • [1] Babasinian V.S., 1943, ORG SYNTH, V2, P466
  • [2] 2-NITRO-THIOPHENE,3-NITRO-THIOPHENE,2,4-DINITRO-THIOPHENE, AND 2,5-DINITROTHIOPHENE
    BLATT, AH
    BACH, S
    KRESCH, LW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (12) : 1693 - 1695
  • [3] BROWN TA, 1967, CHEM BR NOV, P504
  • [4] Butters M., 1992, SOLID SUPPORTS CATAL, P130
  • [5] Clark J.H., 1995, CHEM WASTE MINIMISAT
  • [6] A PROCEDURE FOR QUANTITATIVE REGIOSELECTIVE NITRATION OF AROMATIC-HYDROCARBONS IN THE LABORATORY
    CORNELIS, A
    DELAUDE, L
    GERSTMANS, A
    LASZLO, P
    [J]. TETRAHEDRON LETTERS, 1988, 29 (44) : 5657 - 5660
  • [7] HEIGHTENED SELECTIVITY IN AROMATIC NITRATIONS AND CHLORINATIONS BY THE USE OF SOLID SUPPORTS AND CATALYSTS
    DELAUDE, L
    LASZLO, P
    SMITH, K
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (12) : 607 - 613
  • [8] DINGLE LE, 1968, CHEM BR, P136
  • [9] FISHER A, 1964, J CHEM SOC, P3691
  • [10] APPLICATION OF H-ZSM-5 ZEOLITE FOR REGIOSELECTIVE MONONITRATION OF TOLUENE
    KWOK, TJ
    JAYASURIYA, K
    DAMAVARAPU, R
    BRODMAN, BW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) : 4939 - 4942