Synthetic method of p-acetoxystyrene

A technology of acetoxystyrene and acetoxybromobenzene is applied in the field of synthesis of p-acetoxystyrene, can solve the problems of low yield, difficult availability of reaction raw material p-acetoxyphenethyl alcohol, etc. High efficiency, mild reaction conditions and less environmental pollution

Pending Publication Date: 2021-02-26
惠泽化学科技(濮阳)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the method is simple in steps, the reaction raw material p-acetoxyphenethyl alcohol is not easy to obtain, and the yield is not high, lower than 78%.

Method used

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  • Synthetic method of p-acetoxystyrene
  • Synthetic method of p-acetoxystyrene
  • Synthetic method of p-acetoxystyrene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]In a 1L reaction flask, add 450g ethyl acetate, p-bromophenol (86.5g, 0.5mol), and sodium carbonate (63.6g, 0.6mol) in sequence. Turn on the stirring, keep the temperature at 0°C, and add acetyl chloride (58.8 g, 0.75 mol) dropwise. After the dripping is completed, continue to heat and stir for 8 hours, wash 3 times with water, stand for separation, and distill the organic layer to recover the solvent to obtain 98 g of light brown liquid, namely 4-acetoxybromobenzene, with a yield of 91%. The purity is 96.0%.

[0039]Add 4-acetoxybromobenzene (107.5g, 0.5mol), vinylboronic acid (39.5g, 0.55mol), palladium tetrakistriphenylphosphine (2.9g, 2.5mmol), sodium phosphate (163.9g) into the reaction flask , 1.0mol), ethanol (500mL), mix and stir. Then, the reaction was carried out at 100°C for 12 hours. After the reaction is completed, cool to room temperature, wash with water and stand for separation. The organic phase is dried over anhydrous magnesium sulfate overnight. After filtratio...

Embodiment 2

[0042]In a 2L reaction flask, add 600g of dichloromethane, p-bromophenol (86.5g, 0.5mol), and triethylamine (65.7g, 0.65mol) in sequence. Turn on the stirring, keep the temperature at 10°C, and add acetyl chloride (51 g, 0.65 mol) dropwise. After the dropwise addition is completed, after stirring for 6 hours at room temperature, wash with 10% sodium bicarbonate aqueous solution for 3 times, stand for layering, separate the organic phase, dry over anhydrous magnesium sulfate overnight, filter the organic layer and distill the solvent to obtain 101g The light brown liquid is 4-acetoxybromobenzene with a yield of 94% and a purity of 96.5%.

[0043]Add 4-acetoxy bromobenzene (107.5g, 0.5mol), vinyl borate (101.4g, 0.6mol), palladium acetate (0.9g, 4mmol), potassium carbonate (82.9g, 0.6mol) into the reaction flask ), dichloroethane (500 mL). Mix and stir, and then react for 24 hours at 80°C. After the reaction is completed, it is cooled to room temperature, washed with water and left for s...

Embodiment 3

[0045]In a 500mL reaction flask, p-bromophenol (86.5g, 0.5mol) and acetic anhydride (61.2g, 0.6mol) were sequentially added, and the reaction was stirred for 2h while maintaining the temperature at 180°C. After the completion of the reaction, vacuum distillation was performed to obtain 102 g of a reddish brown oily liquid, namely 4-acetoxybromobenzene, with a yield of 95% and a purity of 95.8%.

[0046]Add 4-acetoxybromobenzene (107.5g, 0.5mol), potassium ethylene trifluoroborate (87.1g, 0.65mol) and [1,1'-bis(diphenylphosphino)ferrocene into the reaction flask ] Palladium dichloride (3.9g, 5mmol), sodium carbonate (127.2g, 1.2mol), dimethylformamide (500mL), mixed and stirred, and then reacted at 100°C for 8 hours. After the reaction is completed, cool to room temperature, wash with water and stand for separation. After the organic phase is dried over anhydrous magnesium sulfate, it is distilled to obtain 74.2g of colorless liquid, namely p-acetoxystyrene, with a yield of 91% and a pu...

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Abstract

The invention discloses a synthesis method of p-acetoxystyrene, which comprises the following steps: carrying out acetylation reaction on p-bromophenol to generate 4-acetoxybromobenzene, and reactingthe 4-acetoxybromobenzene with a vinyl boric acid compound to obtain p-acetoxystyrene. The method is mild in reaction condition, high in yield, environmentally friendly and suitable for industrial production.

Description

Technical field[0001]The invention belongs to the field of chemical synthesis, and specifically relates to a method for synthesizing p-acetoxystyrene.Background technique[0002]Photoresist, also known as photoresist, is a light-sensitive mixed liquid composed of three main components: photosensitive resin, sensitizer (see spectral sensitizing dye) and solvent. After the photosensitive resin is exposed to light, the photocuring reaction can occur quickly in the exposed area, which makes the physical properties of this material, especially the solubility and affinity, change significantly. After proper solvent treatment, the soluble part is dissolved to obtain the desired image. 248nm deep ultraviolet photoresist is currently the mainstream photoresist product in the world, and it is one of the key materials for photoetching integrated circuits and chip manufacturing. The main component of this photoresist is poly(p-hydroxystyrene). In addition to its application in the field of microe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/293C07C69/157
CPCC07C67/293C07C69/157
Inventor 刘显伟马青松吴国印刘娇王晓莹马心旺
Owner 惠泽化学科技(濮阳)有限公司
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