高等学校化学学报

高等学校化学学报 ›› 1991, Vol. 12 ›› Issue (4): 491.

• 论文 • 上一篇    下一篇

相转移催化下4-氯苯磺酰基乙酸异丙酯的烷基化反应

张立康, 张正   

  1. 南京大学化学系, 210008
  • 收稿日期:1989-11-30 出版日期:1991-04-24 发布日期:1991-04-24
  • 通讯作者: 张正

Alkylation of Isopropyl 4-Chlorobenzenesulfonyl Acetate Under Phase Transfer Catalysis Condition

Zhang Li-kang, Zhang Zheng   

  1. Deyartment of Chemistry, Nanjing Universitg, Nanjing, 210008
  • Received:1989-11-30 Online:1991-04-24 Published:1991-04-24

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摘要： 在有机合成中可用芳磺酰基作暂时性活化基团。芳磺酰基乙酸酯是具有活性亚甲基的弱酸性化合物。通常要在氢化钠、醇钠存在下才能起烷基化反应。Ono等曾报道4-甲苯磺酰基乙酸甲酯在DBu存在下进行烷基化反应,但反应时间长。近年来,相转移催化在有机反应中的应用受到重视,然而用固液相转移催化法使芳磺酰基乙酸酯起烷基化反应还未见报道。我们在K2CO3/DMF体系中,用TEBA作催化剂,研究了4-氯苯磺酰基乙酸异丙酯与不同类型卤代烃所起的烷基化反应。合成了尚未见报道的一或二烷基化产物。

关键词: 相转移催化, 烷基化反应, 4-氯苯磺酰基乙酸异丙酯

Abstract: Alkylation of isopropyl 4-chlorobenzenesulfonyl acetate (1) with alkyl halides R1X(R1=n-Bu, CH2=CHCH2, p-CiC6H4CH2, C6H5CH2CH2, C6H5CH2; X=Cl, Br) in the system of K2CO3/DMF was carried out under solid-liquid phase transfer catalysis and five α-substituted products (2a-e) were obtained. The monoalkylated products directly reacted with active alkyl halides R2X (R2: CH2=CHCH2, p-ClC6H,CH2, C6H;CH2; X=Cl, Br) in one-pot to give dialkylated compounds 3n-t. This method has the advantage of moderate reaction conditions and high yields.

Key words: Phase transfer catalysis, Alkylation, Isopropyl 4-chlorobenzenesulfonyl acetate

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