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Synthesis of 2-methoxyl-5-iodophenol

A synthesis method, a methoxyl technology, applied in the direction of organic chemistry, etc., can solve the problems of poor separation effect, unsuitable for industrial production, expensive reagents, etc., and achieves few steps, positioning effect and easy separation of products, and cheap reagents. Effect

Inactive Publication Date: 2005-12-14
SHANGHAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The positioning effect of the benzene ring of this route is slightly better than that of the first one, but its separation effect is poor, and the reagents used are more expensive, so it is not suitable for industrial production

Method used

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  • Synthesis of 2-methoxyl-5-iodophenol
  • Synthesis of 2-methoxyl-5-iodophenol
  • Synthesis of 2-methoxyl-5-iodophenol

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Embodiment 1

[0019] Embodiment one: the specific steps of this embodiment are as follows:

[0020] 1. Synthesis of p-toluenesulfonic acid-(2-methoxy)phenol ester:

[0021] Take 30 grams of 2-methoxy-phenol and dissolve it in 300 ml of triethylamine. After stirring evenly, add an equivalent amount of p-toluenesulfonyl chloride, control the temperature below 15°C and continue stirring for 6 hours, and let it stand overnight. After filtering, the obtained solid was washed twice with triethylamine and water respectively to obtain 63 g of white solid with a yield of 93.3% and a melting point of 82.1-82.3°C. Infrared IR: 3003cm -1 , 1597cm -1 , 1499cm -1 , 1257cm -1 , 1185cm -1 , 867cm -1 , 781cm -1 , 758cm -1 . NMR 1 H-NMR (CDCl 3 )δ: 7.52 (dd, 4H), 7.16 (m, 2H), 6.88 (m, 2H), 3.55 (s, 3H), 2.44 (s, 3H).

[0022] 2. Synthesis of p-toluenesulfonic acid-(2-methoxy-5-iodo)phenol ester:

[0023] Weigh 33 grams of (2-methoxy)phenol p-toluenesulfonate, dissolve it in 200 milliliters of g...

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Abstract

The present invention relates to the synthesis process of 2-methoxyl-5-iodophenol. The synthesis process includes the following steps: the reaction of 2-methoxyl-phenol and p-toluenesulfonyl chloride in triethylamine solvent to prepare p-toluenesulfo-(2-methoxyl) phenol ester; the reaction of p-toluenesulfo-(2-methoxyl) phenol ester, metal chloride and iodine monochloride to produce great amount of solid; suction filtering, washing with glacial acetic acid and water washing to obtain p-toluenesulfo-(2-methoxyl-5-iodo) phenol ester; and final deprotection of p-toluenesulfo-(2-methoxyl-5-iodo) phenol ester to obtain 2-methoxyl-5-iodophenol. The present invention has the advantages of simple operation, low material cost, high yield, high product purity, etc. and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing 2-methoxyl-5 iodophenol. Background technique [0002] The discotic liquid crystal with triphenylene as the skeleton is a potential one-dimensional organic conductor optoelectronic material, which has extremely important application and development prospects. Among them, 2-methoxy-5-iodophenol is an important intermediate for the synthesis of discotic liquid crystals, and has important industrial development prospects. [0003] In the current prior art, the synthesis of 2-methoxy-5 iodophenol mainly contains the following two methods [0004] One: a rough synthetic route proposed by Neville Boden et al. in 1994. In this route, 2-methoxyphenol is first protected by acetylation with acetyl chloride, then halogenated, and then deprotected. The synthetic route of NevilleBoden is as follows: [0005] [0006] This synthetic route has the disadvantages of low yield, many by-products, and difficult sepa...

Claims

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Application Information

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IPC IPC(8): C07C43/253
Inventor 万文王朋玉袁忠谦
Owner SHANGHAI UNIV
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