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Method for synthesizing 2-hydroxymethyl acrylate compound

A technology of methylol acrylate and acrylate, applied in the field of synthesis of 2-hydroxymethylacrylate compounds, can solve problems such as slow reaction speed and low reaction yield, achieve easy operation and reduce acetal side reactions , the effect of reducing production costs

Inactive Publication Date: 2010-07-21
INSIGHT HIGH TECH (BEIJING) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The object of the invention is to provide a kind of synthetic method of 2-hydroxymethyl acrylate compound, carry out the synthetic of product with improved Baylis-Hillman reaction, this method has overcome traditional Baylis-Hillman reaction speed is slow, and reaction yield is low question

Method used

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  • Method for synthesizing 2-hydroxymethyl acrylate compound
  • Method for synthesizing 2-hydroxymethyl acrylate compound

Examples

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Embodiment 1

[0016] Embodiment 1: the synthesis of ethyl 2-hydroxymethacrylate

[0017] Add 33.4g of paraformaldehyde, 60g of water, and 1.7ml of phosphoric acid (1mol / L) into a 250ml reaction bottle, seal and stir to heat up to 95°C, react for 4 hours, and cool to room temperature for later use. Add 100g of ethyl acrylate, 16.7g of DABCO, 0.08g of p-methoxyphenol, and 100ml of THF into a 1000ml reaction bottle, stir at room temperature until completely dissolved, then add the prepared formaldehyde solution, and add 3ml of 30% sodium hydroxide solution at a uniform speed, Adjust the pH of the system to be alkaline. Stir for 4.5 hours for post-treatment: add 20 g of sodium chloride to saturate the aqueous phase, adjust the pH to 7 with hydrochloric acid, separate the liquids, add 20 g of anhydrous sodium sulfate to the organic phase, stir for 2 hours, and filter. After removing the solvent, the filtrate was distilled under reduced pressure, and the fraction at 120-122°C / 130Pa was received ...

Embodiment 2

[0018] Embodiment 2: the synthesis of 2-hydroxypropyl methacrylate

[0019] Add 45g of paraformaldehyde, 80g of water, and 2.3ml of phosphoric acid (1mol / L) into a 250ml reaction bottle, seal and stir to heat up to 80°C, react for 4 hours, and cool to room temperature for later use. Add 100g of propyl acrylate, 9.6g of DABCO, and 100ml of THF into a 1000ml reaction bottle, stir at 50°C until completely dissolved, add the prepared aqueous formaldehyde solution, add 4ml of 30% potassium hydroxide solution, adjust the pH of the system to be alkaline, and stir for 6 hours Post-treatment: add 20 g of sodium chloride to saturate the aqueous phase, adjust the pH value to 7 with hydrochloric acid, separate the liquids, add 20 g of anhydrous sodium sulfate to the organic phase, stir for 2 hours, and filter. After removing the solvent, the filtrate was distilled under reduced pressure to obtain 115 g of 2-hydroxypropyl methacrylate with a purity of 99.0% and a yield of 88.5%.

Embodiment 3

[0020] Embodiment 3: the synthesis of 2-methyl hydroxymethacrylate

[0021] Add 45g of paraformaldehyde, 80g of water, and 2.3ml of 1mol / L phosphoric acid into a 250ml reaction bottle, seal and stir to heat up to 95°C, react for 4 hours, and cool to room temperature for later use. Add 86g of methyl acrylate, 9.6g of DABCO, and 100ml of THF into a 1000ml reaction bottle, stir until completely dissolved at 80°C, add the prepared aqueous formaldehyde solution at 85°C, add 4ml of 30% sodium carbonate solution, and adjust the pH of the system to be alkaline. Stir for 8 hours for post-treatment: add 20 g of sodium chloride to saturate the aqueous phase, adjust the pH to 7 with hydrochloric acid, separate the liquids, add 20 g of anhydrous sodium sulfate to the organic phase, stir for 2 hours, and filter. After removing the solvent, the filtrate was distilled under reduced pressure, and the fraction received was 110-112° C. / 130 Pa to obtain 95 g of methyl 2-hydroxymethacrylate with a...

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Abstract

The invention discloses a method for synthesizing a 2-hydroxymethyl acrylate compound, which is characterized by dropwise adding the aqueous solution of formaldehyde into THF solution of acrylate and a catalyst triethylenediamine (DABCO), stirring the mixture to react, adjusting the pH value of the system in the process of reaction, after reaction, obtaining the product through post-treatment. The method effectively improves the defect that the traditional Baylis-Hillman reaction is slow and low in product yield, and has the characteristics of simple operation, low production cost, short production cycle, good product quality, etc.

Description

technical field [0001] The invention relates to a method for synthesizing 2-hydroxymethacrylate compounds. The compound can be used for synthesizing pharmaceutical intermediates and high sugar compounds. Background technique [0002] 2-Hydroxymethacrylate compounds (Formula 1) are an important class of organic intermediates, not only for the synthesis of intermediates with anticancer active drugs, but also for the synthesis of high-sugar compounds. [0003] Formula 1 [0004] Most of the synthesis of 2-hydroxymethyl acrylates adopts the Baylis-Hillman reaction, which is formed by reacting acrylate and paraformaldehyde as raw materials under the action of an appropriate catalyst. The Baylis-Hillman reaction is a reaction that can efficiently form C-C bonds under mild conditions. Due to its atom economy and the formation of multifunctional products, it is widely used in biologically active compounds. However, the reaction has problems such as slow speed and low reaction y...

Claims

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Application Information

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IPC IPC(8): C07C69/732C07C67/31
Inventor 赵文超陈东阳麻忠利
Owner INSIGHT HIGH TECH (BEIJING) CO LTD
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