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Preparation method of p-acetoxystyrene

A technology of acetoxystyrene and acetoxyacetophenone, which is applied in the field of preparation of p-acetoxystyrene, can solve the problems of complex process, low yield, expensive reagents, etc.

Inactive Publication Date: 2020-01-07
上海万溯药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Above these methods, exist or reagent is expensive, or process is complicated, or the deficiencies such as low yield

Method used

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  • Preparation method of p-acetoxystyrene
  • Preparation method of p-acetoxystyrene

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[0049] The invention provides a kind of preparation method of acetoxystyrene, comprising:

[0050] 1) reacting p-hydroxyacetophenone with an acetylating reagent to prepare p-acetoxyacetophenone;

[0051] 2) Hydrogenating and reducing p-acetoxyacetophenone to prepare 1-(4-acetoxyphenyl)ethanol;

[0052] 3) Eliminate 1-(4-acetoxyphenyl)ethanol to prepare p-acetoxystyrene.

[0053] The preparation method of acetoxystyrene provided by the present invention may include an acetylation reaction, and the acetylation reaction may specifically include: reacting p-hydroxyacetophenone with an acetylating reagent to prepare p-acetoxyacetophenone , the reaction equation is as follows:

[0054]

[0055] In the present invention, in the acetylation reaction, the reaction is usually carried out in the presence of an acid-binding agent, thereby providing alkaline reaction conditions and neutralizing the acid generated during the reaction. Those skilled in the art can select the appropriat...

Embodiment 1

[0077] Synthesis of p-acetoxyacetophenone:

[0078] In a 10L reaction flask, add 4080g of ethyl acetate, 1360g of p-hydroxyacetophenone, and 1272g of sodium carbonate in sequence, start stirring, and add 1335g of acetyl chloride dropwise at a temperature of 20-30°C. After the dropwise addition was completed, continue to insulate and stir for 8 hours, filter, and the filtrate was washed and layered with 3022g of 8% aqueous sodium bicarbonate solution, and the organic layer was distilled to reclaim the solvent, and 1380g of hexane was added to the concentrated residue, filtered after stirring and crystallizing, and filtered. After the cake was dried, 1660 g of p-acetoxyacetophenone was obtained, and the HPLC purity was >99.9%. 1 H NMR (400MHz, (CD 3 ) 2 SO): δ = 2.31 (s, 3H), 2.59 (s, 3H), 7.29 (d, J = 8.8, 2H), 8.02 (d, J = 8.8, 2H). 13 C NMR (100MHz, (CD 3 ) 2 SO): δ=21.34, 27.18, 122.58, 128.99, 134.89, 154.59, 169.31, 197.36.

Embodiment 2

[0080] Synthesis of p-acetoxyacetophenone:

[0081] In a 1000mL reaction flask, add 390g of dichloromethane, 130g of p-hydroxyacetophenone, and 116g of triethylamine in sequence, start stirring, and add 108g of acetyl chloride dropwise at a temperature of 30-40°C. After the dropwise addition was completed, the insulation and stirring were continued for 6 hours, then 260 g of water was added, and after stirring for 0.5 hours, layers were separated. 130g of water was added to the organic layer, and adjusted to neutral with sodium bicarbonate, the solvent was recovered by distillation of the layered organic layer, 130g of hexane was added to the concentrated residue, stirred and crystallized, and then filtered, and the filter cake was dried to obtain 150g of para-acetoxy Acetophenone, HPLC purity 99.5%.

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Abstract

The invention relates to the field of organic chemistry, and in particular, relates to a preparation method of p-acetoxystyrene. The preparation method of p-acetoxystyrene provided by the invention comprises the steps: carrying out a reaction of p-hydroxyacetophenone with an acetylation reagent to prepare p-acetoxyacetophenone; carrying out hydrogenation reduction on p-acetoxyacetophenone to prepare 1-(4-acetoxyphenyl)ethanol; and carrying out an elimination reaction on 1-(4-acetoxyphenyl)ethanol to prepare p-acetoxystyrene. According to the preparation method of p-acetoxystyrene, starting from the most basic raw materials, three steps of reactions are carried out, especially in the third step of alkene formation reaction, alkaline elimination is creatively adopted, the defects that in traditional acid catalysis alkene formation elimination reaction, double-bond acid catalysis sudden side reactions are likely to happen, the reaction is likely to be out of control, and consequently theyield is low are overcome, and generated double bonds can stably exist for a long time in a reaction system.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a preparation method of p-acetoxystyrene. Background technique [0002] Poly(p-hydroxystyrene) can be used in chemical adhesives, coatings and other material chemistry fields, especially in the fields of integrated circuit etching and chip manufacturing. It is the main component of chemically amplified photoresist. p-Acetoxystyrene is an important monomer compound for the synthesis of poly(p-hydroxystyrene). [0003] The known synthetic methods of p-acetoxystyrene mostly use p-hydroxybenzaldehyde or p-hydroxyacetophenone as raw materials and synthesize them through multi-step reactions. The methods described in patents US4316995, US2004118673, US2005228191, etc. are that p-hydroxybenzaldehyde and malonic acid are reacted to synthesize styrene dicarboxylic acid intermediate, and then acetoxystyrene is obtained through two steps of decarboxylation and acetylation. The method prov...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/14C07C67/29C07C67/28C07C69/157
CPCC07C67/14C07C67/28C07C67/29C07C69/157
Inventor 杨东孙元健何立袁云龙
Owner 上海万溯药业有限公司
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