高等学校化学学报

高等学校化学学报 ›› 1997, Vol. 18 ›› Issue (12): 1987.

• 论文 • 上一篇    下一篇

(Z)-3-丁烯基-5-羟基苯酞的合成

李绍白, 王志伟   

  1. 兰州大学应用有机化学国家重点实验室, 兰州 730000
  • 收稿日期:1996-08-29 出版日期:1997-12-24 发布日期:1997-12-24
  • 通讯作者: 李绍白, 男, 50岁, 副研究员.
  • 作者简介:李绍白, 男, 50岁, 副研究员.
  • 基金资助:

    国家自然科学基金

Synthesis of 3-Butylidene-5-hydroxyphthalide

LI Shao-Bai, WANG Zhi-Wei   

  1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000
  • Received:1996-08-29 Online:1997-12-24 Published:1997-12-24

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被引次数

2

摘要： 以对羟基苯甲酸为原料,首次合成(Z)-3-丁烯基-5-羟基苯酞．发现芳环上的甲胺甲酸基中氮原子的诱导作用是关键步骤,使甲胺甲酸基邻位选择性理化,从而在芳环上定向引入甲酸基．

关键词: (Z)-3-丁烯基-5-羟基苯酞, 苯酞, 合成

Abstract: 3-Butylidene-5-hydroxyphthalide (1), isolated from Ligusticum wallichii., hasbeen first syntheslzed starting from 4-hydroxybenzoic acid in 8 steps.Herein compound 4 ondirected matallation with n-butyllithium in the presence of TMEDA followed by treatmentwith DMFgave 5 in 80% yield.The hydrolysis of 5 by employing 4 mol HCl aq.gave 6 in 83% yield.Compound 6 was converted to the acid (7) by the conventional method.Com-pound 7 was dissolved in sodium bicarbonate and reacted with a solution of iodine in aqueouspotassium iodide to give 8.Iodophthalide (8) was reacted with sodium acetate in refluxingethanol to furnish 9 in 94% yield- Demethylation of 9 was conducted in methylene chloridewith boron tribromide to give the title compound(1).The spectral data of 1 are consistentwith those of the natural product.

Key words: (Z)-3-Butylidene-5-hydroxyphthal, Phthalide, Synthesis

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