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Preparation method of 2-hydroxymethyl methyl acrylate

A technology of methyl hydroxymethyl acrylate and methyl bromoacetate, which is applied in the field of preparation of 2-methyl hydroxy methacrylate, can solve the problems of large amount of "three wastes", low product purity, and many impurities, and achieve production costs Low, high product yield effect

Inactive Publication Date: 2017-01-18
启东东岳药业有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] This method is simple and convenient, but the amount of "three wastes" is large, the product purity is low, and there are many impurities

Method used

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  • Preparation method of 2-hydroxymethyl methyl acrylate
  • Preparation method of 2-hydroxymethyl methyl acrylate
  • Preparation method of 2-hydroxymethyl methyl acrylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] One, the preparation of methoxycarbonyl methylene triphenylphosphonium bromide:

[0033] Add 88g (0.29mol) triphenylphosphine to the three-necked flask, add 200ml toluene to dissolve, then dissolve 4.8g (0.029mol) KI in 200ml water and add toluene, add 44.4g (0.29mol) 2-bromoacetic acid dropwise methyl ester. Under the protection of nitrogen, the temperature was raised to 65-75°C and kept for 20 hours. After the heat preservation is over, cool down to 50-60°C, add 350ml of water, and separate the phases. The water phase was kept at 40°C, and 268.4 grams of 10% sodium hydroxide solution was slowly added dropwise. After the dropping, the solution was kept for 30 minutes, filtered with suction, the filter cake was rinsed with 40ml of n-heptane, and dried under reduced pressure at 50°C to obtain 119.2 grams of a yellow solid. Yield 90%.

[0034] Two, the preparation of 2-hydroxy methyl acrylate:

[0035] Add 119.2 grams of methoxycarbonylmethylene triphenylphosphine bro...

Embodiment 2

[0037] A preparation method of 2-methyl hydroxymethacrylate, comprising the following steps:

[0038] (1) Triphenylphosphine, catalyst and solvent are mixed, 2-methyl bromoacetate is added dropwise in the mixed solution, and the reaction is heated up;

[0039] (2) After the reaction finishes, leave it to stand for phase separation, and separate the toluene phase;

[0040] (3) drip aqueous sodium hydroxide solution, crystallization by cooling;

[0041] (4) suction filtration, rinse filter cake with n-heptane, make methoxycarbonyl methylene triphenyl phosphorus chloride, machine Wittig reagent;

[0042] (5) Add Wittig reagent to water, add formaldehyde aqueous solution, drop potassium carbonate aqueous solution to react;

[0043] (6) remove triphenylphosphine by filtration;

[0044] (7) filtrate is added to solvent extraction;

[0045] (8) Concentrate the organic phase, and distill under reduced pressure after removing the solvent to obtain 2-methyl hydroxymethacrylate.

[...

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Abstract

The invention discloses a preparation method of 2-hydroxymethyl methyl acrylate. The method includes the steps of firstly, mixing triphenyl phosphine, a catalyst and solvent, and dropwise adding 2-methyl bromoacetate to mixed liquid for temperature raising reaction; secondly, after reaction ends, being standing still and separating phases to separate out a methylbenzene phase; thirdly, dropwise adding a sodium hydroxide aqueous solution for cooling and crystallizing; fourthly, conducting suction filtration, and rinsing a filter cake with n-heptane to prepare methoxycarbonyl methylene triphenyl phosphoric chloride, namely a Wittig reagent; fifthly, adding the Wittig reagent to water, adding a formaldehyde aqueous solution, and dropwise adding a potassium carbonate aqueous solution for reaction; sixthly, filtering out triphenyl phosphine; seventhly, adding the solvent to filtrate for extraction; eighthly, concentrating an organic phase, and conducting reduced pressure distillation after removing the solvent to obtain 2-hydroxymethyl methyl acrylate. The raw materials are easy to obtain, production cost is low, and the method is suitable for industrial production and high in product yield.

Description

technical field [0001] The invention relates to a preparation method of 2-methyl hydroxymethacrylate. Background technique [0002] 2-Hydroxymethyl methacrylate is an important pharmaceutical intermediate, which can be used for the new anti-hepatitis B drug telbivudine. The structure of 2-hydroxymethyl methacrylate is as follows: [0003] The structure of methyl 2-hydroxymethacrylate is as follows: [0004] [0005] There are many preparation methods of phenylalaninol. Wherein main preparation method has following two kinds: [0006] Method one (Organic Letters 2006, Vol.83359-3362):. [0007] [0008] The raw material of this method is easy to obtain, but the reaction is very slow, and there are many side reactions, so it is not suitable for industrial production. [0009] Method 2 (Organic synthesis) [0010] [0011] This method is simple and convenient, but the amount of "three wastes" is large, the product purity is low, and there are many impurities. Co...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/732
CPCC07C67/343C07C69/732
Inventor 龙中柱安娜凌晓峰蔡水洪
Owner 启东东岳药业有限公司
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