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Process for synthesizing o-chloro-anisole

A synthesis method and chloroanisole technology are applied in the field of synthesis of fine chemical intermediates, can solve problems such as high price, difficult recycling, environmental pollution, etc., and achieve good industrial application prospects, high product yield, and environmental pollution. small effect

Inactive Publication Date: 2009-04-15
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This reaction requires anhydrous sodium methoxide, which is more expensive, and the HMPA used has a higher boiling point, can be miscible with water in any proportion, is difficult to recycle, and the waste water produced after the reaction is easy to cause serious pollution to the environment

Method used

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  • Process for synthesizing o-chloro-anisole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In the reactor, o-dichlorobenzene (44.1g, 0.3mol), sodium methoxide solution (115.7g, 0.6mol) and N, N-dimethylformamide (100ml) with a mass fraction of 28% were mixed and added CuBr (3g, 0.021mol) was used as a catalyst, and the methanol was distilled under stirring until the kettle temperature reached 135°C and then refluxed for 20 hours; (30ml×3) extraction, and rectification of the organic liquid to obtain 32.2g of the compound o-chloroanisole, with a yield of 75.6%.

[0021] The experimental data are as follows:

[0022] b.p.193-195°C; 1 HNMR (400MHz, CDCl 3 )δ (ppm): 3.82 (s, 3H, OCH 3 ), 6.80-7.17 (m, 4H, ArH); IR (liquid film) cm -1 : 3057, 2999, 2965, 2940, 1583, 1549, 1462, 1300, 1253, 1134, 1026, 941; CI-MS: 142 (M + )

Embodiment 2

[0024] In the reactor, o-dichlorobenzene (58.8g, 0.4mol), a mass fraction of 28% sodium methoxide solution (38.6g, 0.2mol) and N,N-dimethylformamide (100ml) were mixed, and added CuBr (3g, 0.021mol) was used as a catalyst; the methanol was distilled under stirring until the temperature of the kettle reached 135°C and then refluxed for 20 hours; (30ml×3) extraction, and distillation of the organic liquid to obtain 8.1 g of the compound o-chloroanisole, with a yield of 28.5%.

Embodiment 3

[0026] According to the method in Example 1, the feeding amount of the sodium methoxide solution was 231.4 g, and 32.4 g of o-chloroanisole was obtained after the reaction, with a yield of 76.1%.

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Abstract

The invention discloses a method for synthesizing o-chloro anisole, wherein, o-dichlorobenzene is used as raw material which has a substitution reaction with sodium methoxide to get o-chloro anisole, with the presence of catalyst. The raw materials of the synthesis method are industrial side products which are easy to get; in addition, the operation is simple, with little pollution; the production cycle is short; the yield coefficient of the product is higher; and the product has good industrialization application prospect.

Description

technical field [0001] The present invention relates to a kind of synthetic method of fine chemical intermediate, specifically a kind of synthetic method of o-chloroanisole. Background technique [0002] O-chloroanisole (also known as 2-chloroanisole) is an important class of chemical raw materials, widely used in pharmaceutical analysis, lithium battery electrolyte, electrophotographic photosensitive devices and other fields. [0003] Regarding the synthesis of o-chloroanisole, there are generally two synthetic approaches: one is to synthesize o-chloroanisole in the presence of some chlorinating reagents using anisole as a raw material. Such as Masao H. et al. (J.Chem.Soc., PerkinTrans.1, 1997, 3081-3085) reported that in the presence of Mn (III) catalyst, anisole and sodium chlorite react to obtain o-chloroanisole And p-chloroanisole, its ratio is 1: 9, and this method reaction selectivity is poor, is often based on p-chloroanisole, and yield is not high; The reaction gi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/225C07C41/01
Inventor 朱锦桃宋光伟姚国新陈刚
Owner ZHEJIANG SCI-TECH UNIV
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