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Method for synthesizing 4-methoxy styrene

A technology of methoxystyrene and methoxyacetophenone, which is applied in the field of synthesis of 4-methoxystyrene, can solve the problems of cumbersome preparation of raw material amides, unsuitability for industrial production, and many olefin by-products. The effect of cheap raw materials, high yield, and easy availability of raw materials

Inactive Publication Date: 2005-08-31
SHANGHAI UNIV
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Problems solved by technology

Grignard reagents require the reaction system to be strictly anhydrous during preparation and use, and the raw materials used in this method are substituted benzaldehyde and methyl Grignard reagents, which are expensive and not suitable for industrial production
[0010] (2) Substituted benzaldehyde and Wittig reagent react to prepare substituted styrene (Polymer, 1983,24,995), although this method has one step less than using the Grignard reagent method in the synthetic steps, the disadvantage is similar to the use of Grignard Reagents are similar to
[0014] (2) Aslam etc. made the alcohol obtained by reducing the substituted acetophenone through intermolecular condensation reaction to make ether first, and then dehydrated the ether to also make substituted styrene (US 5194672). This method dehydrates the alcohol to generate olefins into two It is a good method to overcome the disadvantage of directly generating olefin by-products in one step.
The preparation of raw material amides is also more cumbersome

Method used

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  • Method for synthesizing 4-methoxy styrene

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Embodiment 1

[0029] Embodiment one: now the concrete process step of the inventive method is described as follows:

[0030] a. Reduction reaction: Add 1 kilogram (6.659 moles) of 4-methoxyacetophenone in a 5-liter round-bottomed flask, 2 liters of industrial alcohol, stir, and after dissolving, add 120 grams of potassium borohydride (2.224 mol), while keeping the reaction temperature at 20°C-40°C, react for 6 hours. After the reaction, add an equal volume of water and stir well to hydrolyze excess potassium borohydride and borate complex. Then, 2 liters of ethyl acetate was added for extraction, and the layers were separated to obtain an organic layer. The aqueous layer was extracted twice with a small amount of ethyl acetate, and the organic layers were combined. Use anhydrous magnesium sulfate to dry, spin dry solvent with rotary evaporator again, obtain 0.993 kilograms of product 1-(4'-methoxyphenyl) ethanol, productive rate 98% (productive rate is based on raw material 4-methoxyphenyl...

Embodiment 2

[0033] Embodiment two: present embodiment is substantially the same as embodiment one, and difference is that in step a, the amount of potassium borohydride used is 72 grams (1.332 moles), then the reaction time of step a is extended to 12 hours, 0.801 kg of the product 1-(4'-methoxyphenyl)ethanol was obtained with a yield of 79%. The final product 4-methoxystyrene obtained was 0.617 kg, with a total yield of 69.0%.

Embodiment 3

[0034] Embodiment three: present embodiment is substantially the same as embodiment one, and difference is, in step a, the amount of potassium borohydride used is 180 grams (3.329 mole), then the reaction time of step a is shortened to 4 hours, 0.989 kg of the product 1-(4'-methoxyphenyl)ethanol was obtained with a yield of 98%. The final product 4-methoxystyrene obtained was 0.758 kg, with a total yield of 84.8%.

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Abstract

A process for synthesizing 4-methoxy styrene includes reductive reaction of 4-methoxy acetophenone to obtain 4-(4'-methoxyphenyl) ethanol, esterifying reaction to obtain 1-(4'-methoxyphenyl) ethyl sulfonate, abate reaction to obtain 4-methoxy styrene, and vacuum rectifying.

Description

technical field [0001] The present invention relates to a kind of synthetic method of 4-methoxystyrene. Background technique: [0002] Substituted styrene is a very important class of chemical raw materials, widely used in materials, pharmaceutical intermediates, adhesives, coatings, sunscreens and other fields. This type of compound is easy to polymerize, either homopolymerized or copolymerized, and various polymer materials with different molecular weights can be obtained by different polymerization methods. These polymer materials often show better performance than polystyrene. For example, the coating made of substituted polystyrene has better water and oil displacement than ordinary polystyrene (EP 541395). In addition, polymers substituted for styrene can also be used to make liquid crystal materials (JP 08271739). Among these substituted styrene compounds, a very important compound is 4-methoxystyrene. With the development of the information industry, the degree of...

Claims

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Application Information

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IPC IPC(8): C07C41/18C07C43/243
Inventor 郝健刘义平宋小龙彭荣达毛永浩贾学顺
Owner SHANGHAI UNIV
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