Efficient Flow Synthesis of Glycidyl Ether Using BuSnCl 3 as a Mild Lewis Acid

被引:0
作者
Kasakado, Takayoshi [1 ]
Nakamura, Masahito [2 ]
Nishizawa, Akihiro [3 ]
Hosomi, Tetsuya [3 ]
Ryu, Ilhyong [1 ,4 ]
Fukuyama, Takahide [2 ]
机构
[1] Osaka Metropolitan Univ, Org Res Promot, Sakai, Osaka 5998531, Japan
[2] Osaka Metropolitan Univ, Grad Sch Sci, Dept Chem, Osaka 5588585, Japan
[3] Nagase ChemteX Corp, Tatsuno, Hyogo 6794124, Japan
[4] Natl Yang Ming Chiao Tung Univ NYCU, Dept Appl Chem, Hsinchu 30010, Taiwan
来源
SYNTHESIS-STUTTGART | 2024年 / 56卷 / 20期
基金
日本学术振兴会;
关键词
flow synthesis; glycidyl ethers; epichlorohydrin; BuSnCl (3); Lewis acids; chlorohydrin; CATION-BINDING; EPOXY; POLYMERIZATION; TRANSITION; CATALYSTS; EPOXIDES; ALCOHOL; EUGENOL; REACTOR; RESIN;
D O I
10.1055/a-2359-8893
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A ring-opening protocol of epichlorohydrin with 2-ethylhexanol was investigated for the synthesis of the corresponding chlorohydrin ether. BuSnCl3 proved to be an efficient mild Lewis acid catalyst, yielding the product with high selectivity. A scalable flow synthesis was achieved by modifying the flow setup. The flow synthesis of the corresponding glycidyl ether from the chlorohydrin ether was also carried out in an efficient manner by using the basic treatment.
引用
收藏
页码:3142 / 3146
页数:5
相关论文
共 47 条
  • [1] Acetal-Based Functional Epoxide Monomers: Polymerizations and Applications
    Baek, Jinsu
    Kim, Minseong
    Park, Youngsin
    Kim, Byeong-Su
    [J]. MACROMOLECULAR BIOSCIENCE, 2021, 21 (11)
  • [2] A Perspective on Continuous Flow Chemistry in the Pharmaceutical Industry
    Baumann, Marcus
    Moody, Thomas S.
    Smyth, Megan
    Wharry, Scott
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2020, 24 (10) : 1802 - 1813
  • [3] Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry
    Buglioni, Laura
    Raymenants, Fabian
    Slattery, Aidan
    Zondag, Stefan D. A.
    Noel, Timothy
    [J]. CHEMICAL REVIEWS, 2022, 122 (02) : 2752 - 2906
  • [4] Eugenol, a developing asset in biobased epoxy resins
    Caillol, Sylvain
    Boutevin, Bernard
    Auvergne, Remi
    [J]. POLYMER, 2021, 223
  • [5] Synthesis, characterization, and epoxidation of an aliphatic polycarbonate from 2,2-(2-pentene-1,5-diyl)trimethylene carbonate ((c)HTC) ring-opening polymerization
    Chen, XH
    McCarthy, SP
    Gross, RA
    [J]. MACROMOLECULES, 1997, 30 (12) : 3470 - 3476
  • [6] Investigation of Sn(IV) catalysts in glycerol acetylation
    da Silva, Debora S.
    Altino, Felyppe M. R. S.
    Bortoluzzi, Janaina H.
    Meneghetti, Simoni M. P.
    [J]. MOLECULAR CATALYSIS, 2020, 494
  • [7] Del Vecchio A., 2022, Angew. Chem. Int. Ed, V61, pe202209564
  • [8] CROWN CATION COMPLEX EFFECTS .20. SYNTHESES AND CATION BINDING-PROPERTIES OF CARBON-PIVOT LARIAT ETHERS
    DISHONG, DM
    DIAMOND, CJ
    CINOMAN, MI
    GOKEL, GW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (03) : 586 - 593
  • [9] Photo flow protocol for bromoallylation of alkynes and alkenes
    Fukuyama, Takahide
    Dakegata, Aki
    Ryu, Ilhyong
    [J]. ARKIVOC, 2024,
  • [10] Improved efficiency of photo-induced synthetic reactions enabled by advanced photo flow technologies
    Fukuyama, Takahide
    Kasakado, Takayoshi
    Hyodo, Mamoru
    Ryu, Ilhyong
    [J]. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2022, 21 (05) : 761 - 775