Preparation method of ferrocenecarboxylic acid

A technology of ferrocene formic acid and acetyl ferrocene, applied in chemical instruments and methods, metallocene, organic chemistry, etc., can solve the problems of many by-products, low total yield, and high requirements for experimental equipment, and achieves reaction consumption. Short, easy-to-control, inexpensive effects

Active Publication Date: 2013-10-09
启东市三江建筑机械有限公司
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Problems solved by technology

[0002] Ferrocene formic acid is an important intermediate for the synthesis of ferrocene derivatives with various biological activities. There are three synthetic methods: 1), ferrocene is acylated into acetyl ferrocene, and then reacted with sodium hypochlorite to generate ferrocene Ferrocene formic acid, the total yield of this method is very low, and by-product is more; 2), ferrocene is passed into carbon dioxide direct carboxylation under catalyst action to form ferrocene formic acid at normal pressure, and this method needs to be carried out in dilute solution, However, the requirements for experimental equipment are too high, and the reaction conditions are more difficult to control in the laboratory; 3) ferrocene is reacted with o-chlorobenzoyl chloride to generate o-chlorobenzoyl ferrocene, and then reacted with o-chlorobenzoyl chloride to generate ferrocene Formic acid, the reaction conditions of this method are mild, but the reaction takes too long, and the potassium tert-butoxide used in the experiment is expensive

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  • Preparation method of ferrocenecarboxylic acid

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Embodiment 1

[0022] In the first step, 60 ml of deionized water and 10 grams of sodium hydroxide were added to the reactor to fully stir and dissolve to form a sodium hydroxide solution; the reactor was cooled to 0-5°C in an ice-water bath, and 2 ml of PEG-400 was added under stirring. (polyethylene glycol) and 16.8 grams of iodine-potassium iodide, then add acetylferrocene powder with a total amount of 2.3 grams in four times within 40 minutes, each time adding an equal amount, and then fully stir for 1h;

[0023] In the second step, the solution obtained from the first step was extracted and washed twice with dichloromethane, and the aqueous phase was adjusted to pH=2~3 with strong acid, and a yellow precipitate was formed. After cooling, the solution was filtered and washed twice with water. Ferrocenecarboxylic acid, the yield calculated by weighing is 85.6%. see figure 1 As shown, it is the infrared spectrogram of the solid product obtained in Example 1, and it can be seen from the sp...

Embodiment 2

[0025] In the first step, 60 ml of deionized water and 10 g of sodium hydroxide were added to the reactor to fully stir and dissolve to form a sodium hydroxide solution; the reactor was cooled to 10°C with an ice-water bath, and 2 ml of PEG-400 and 16.8 g iodine-potassium iodide, add acetylferrocene powder with a total amount of 2.76 g in batches within 40 minutes, and then fully stir for 1 h;

[0026] In the second step, the solution obtained from the first step was extracted and washed twice with dichloromethane, and the aqueous phase was adjusted to pH=2~3 with strong acid, and a yellow precipitate was formed. After cooling, the solution was filtered and washed twice with water. Ferrocenecarboxylic acid, 84% yield by weight.

Embodiment 3

[0028] In the first step, 60 ml of deionized water and 10 g of sodium hydroxide were added to the reactor to fully stir and dissolve to form a sodium hydroxide solution; the reactor was cooled to 30°C with an ice-water bath, and 2 ml of PEG-400 and 16.8 g iodine-potassium iodide, add acetylferrocene powder with a total amount of 3.22 g in batches within 40 minutes, and then fully stir for 1 h;

[0029] In the second step, the solution obtained from the first step was extracted and washed twice with dichloromethane, and the aqueous phase was adjusted to pH=2~3 with strong acid, and a yellow precipitate was formed. After cooling, the solution was filtered and washed twice with water. Ferrocenecarboxylic acid, the yield calculated by weighing is 79.3%.

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Abstract

The invention relates to a preparation method of ferrocenecarboxylic acid, comprising the following steps of: firstly, adding polyethylene glycol, iodine-potassium iodide and acetylferrocene into an aqueous alkali with uniformly stirring, wherein the acetylferrocene undergoes an iodoform reaction to form ferrocene carboxylic acid salt dissolved in a non-organic phase; secondly, extracting the solution obtained from the reaction of the first step by the use of an organic solvent, adjusting the pH value of a water phase to 2-3 by the use of strong acid to change sodium ferrocene carboxylic acid into ferrocenecarboxylic acid precipitated from the water phase. According to the invention, non-organic aqueous alkali is used as a solvent to prepare ferrocenecarboxylic acid. The preparation method provided by the invention is easy to control. During the process, the mild reaction is carried out in a solution with the reaction temperature being from zero to 5 DEG C for a short time; ferrocenecarboxylic acid can be produced only within 2 hours. The used raw materials are commonly sold in the market and are cheap. The yield of the product in the invention can reach more than 85% by optimum technology.

Description

【Technical field】 [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing ferrocene formic acid. 【Background technique】 [0002] Ferrocene formic acid is an important intermediate for the synthesis of ferrocene derivatives with various biological activities. There are three synthetic methods: 1) acylation of ferrocene to acetylferrocene, and then reacting with sodium hypochlorite to generate ferrocene ferrocene formic acid, the method total yield is very low, and by-products are many; 2), ferrocene is directly carboxylated into carbon dioxide under the action of a catalyst at atmospheric pressure to form ferrocene formic acid, the method needs to be carried out in a dilute solution, But the requirements for experimental equipment are too high, and the reaction conditions are difficult to control in the laboratory; 3) ferrocene is reacted with o-chlorobenzoyl chloride to generate o-chlorobenzoyl ferrocene, and then react with f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F17/02
Inventor 刘玉婷苏宝君尹大伟廉桂丹冯丽元方
Owner 启东市三江建筑机械有限公司
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