Preparation method and application of p-tert-pentyloxystyrene
Patent Information
- Application Number
- CN202511524001.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-10-23
- Publication Date
- 2026-01-16
AI Technical Summary
现有文献鲜少有该化合物合成方法的报道
1、本发明提供的对叔戊氧基苯乙烯的制备方法，该制备方法包括（1）醇类物质和/或酯类物质与4-氟苯甲醛经缩合反应，制备得到中间体化合物I；（2）所述中间体化合物I、叔戊醇钠在反应溶剂中进行取代反应，反应结束后经水解反应制备得到中间体化合物Ⅱ；所述反应溶剂包括叔戊醇；（3）所述中间体化合物Ⅱ经wittig反应，制备得到对叔戊氧基苯乙烯。该制备方法具有合成步骤简单易控、高效、便捷、原料易得、中间体与产品收率高、产品纯度高、易纯化等优点，所制得的对叔戊氧基苯乙烯在高分子合成、电子材料、日化香料及医药研发等领域中具有不可替代的作用，尤其在高性能聚合物和微电子材料领域展现出良好的应用前前景，产品应用前景广阔。
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Abstract
Description
TECHNICAL FIELD
[0001] The present application relates to the technical field of organic synthesis preparation, and particularly relates to a preparation method and application of p-tert-pentyloxy styrene. BACKGROUND
[0002] KrF photoresist (248nm) is a key material for 130nm-28nm process chip manufacturing. Among them, the resin as the core raw material directly determines the resolution, sensitivity and process compatibility of the photoresist and so on. Different resins also directly affect the performance of the photoresist.
[0003] Resin monomer is the "gene" of KrF photoresist resin, and its core role is to build the matrix structure of the photoresist resin and determine the key performance. The diversity of styrene series resin monomers is the basis for different types of photoresist resins.
[0004] P-tert-pentyloxy styrene is one of styrene series resin monomers, and its main uses include high polymer synthesis, electronic materials, daily chemical perfumes and pharmaceutical research and development and the like. The polymer has a high glass transition temperature, is soluble in aliphatic hydrocarbons, has low volatility, and can provide more basis for the diversity of photoresist resins, and plays an important role in the development of new materials, theoretical research, dispersion polymerization and the like, and has a broad application prospect. There are few reports on the synthesis method of the compound in the existing literature. SUMMARY
[0005] In order to solve the above problems, the present application provides a p-tert-pentyloxy styrene and a preparation method and application thereof.
[0006] In a first aspect, the present application provides a preparation method of p-tert-pentyloxy styrene, comprising the following steps: (1) an alcohol substance and / or an ester substance is subjected to a condensation reaction with 4-fluorobenzaldehyde to prepare an intermediate compound I; (2) the intermediate compound I and sodium tert-pentoxide are subjected to a substitution reaction in a reaction solvent, and after the reaction is completed, an intermediate compound II is prepared through a hydrolysis reaction; the reaction solvent comprises tert-pentanol; (3) the intermediate compound II is subjected to a wittig reaction to prepare p-tert-pentyloxy styrene.
[0007] The present application provides a preparation method of p-tert-pentyloxy styrene, which provides a new preparation method for synthesizing the compound, and the method is simple and easy to operate, and the purity and yield of the product are high.
[0008] In the present application, the step (3), when performing the wittig reaction, adopts the conventional phosphorus ylide reagent in the art, the raw materials of which include but are not limited to at least one of methyltriphenylphosphonium bromide, methyltriphenylphosphonium iodide, methyltriphenylphosphonium chloride, and at least one of potassium tert-butoxide, n-butyllithium, sodium hydride, LiHMDS, NaHMDS, KHMDS, sodium tert-butoxide, cesium carbonate, potassium carbonate, etc.
[0009] The temperature of the wittig reaction is 0-60℃, for example, any one of 0℃, 10℃, 20℃, 30℃, 40℃, 50℃, 60℃, and preferably room temperature.
[0010] As an optional embodiment, the molar ratio of the alcohol and / or ester to the 4-fluorobenzaldehyde is (1.1-1.5):1; for example, any one of 1.1:1, 1.2:1, 1.3:1, 1.4:1, 1.5:1, etc.
[0011] As an optional embodiment, the alcohol includes monohydric alcohol and / or dihydric alcohol; preferably, the monohydric alcohol includes at least one of methanol, ethanol, n-propanol, isopropanol or n-butanol; the dihydric alcohol includes at least one of ethylene glycol, propylene glycol or butanediol; As an optional embodiment, the ester includes at least one of trimethyl orthoformate, triethyl orthoformate or tripropyl orthoformate; As an optional embodiment, the temperature of the condensation reaction is 80-120℃, and the reaction time is 3-8h; for example, any one of 80℃, 90℃, 100℃, 110℃, 120℃, etc. for the temperature, and any one of 3h, 4h, 5h, 6h, 7h, 8h, etc. for the time.
[0012] As an optional embodiment, the catalyst of the condensation reaction includes p-toluenesulfonic acid; preferably, the molar ratio of the 4-fluorobenzaldehyde to the p-toluenesulfonic acid is 1:(0.03-0.2); As an optional embodiment, the reaction solvent of the condensation reaction includes toluene; preferably, the volume ratio of the 4-fluorobenzaldehyde to toluene is 1:(2-8), preferably 1:5.
[0013] As an optional embodiment, the step (1) further includes at least one of quenching, extraction, washing, beating, and reduced pressure filtration after performing the condensation reaction; As an optional embodiment, the step (1) uses a quenching agent to perform the quenching, and the quenching agent includes an aqueous sodium bisulfite solution; As an optional implementation, in the step (1), the volume ratio of the aqueous sodium bisulfite solution to the 4-fluorobenzaldehyde is (4-10):1, preferably 5:1, and the concentration of the aqueous sodium bisulfite solution is 1wt%; for example, the volume ratio of the aqueous sodium bisulfite solution to the 4-fluorobenzaldehyde is any one of 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, etc.
[0014] As an optional implementation, in the step (1), the extraction is performed by using an extraction agent, and the extraction agent includes toluene, and the volume ratio of the toluene to the 4-fluorobenzaldehyde is (4-10):1, preferably 4:1; for example, the volume ratio of the toluene to the 4-fluorobenzaldehyde is any one of 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, etc.
[0015] As an optional implementation, in the step (1), the washing is performed by using a washing agent, and the washing agent includes water, and the volume ratio of the water to the 4-fluorobenzaldehyde is (3-10):1, preferably 4:1; for example, the volume ratio of the water to the 4-fluorobenzaldehyde is any one of 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, etc.
[0016] As an optional implementation, in the step (1), the beating is performed by using n-heptane, and the volume ratio of the n-heptane to the 4-fluorobenzaldehyde is (6-20):1, preferably 8:1; for example, the volume ratio of the n-heptane to the 4-fluorobenzaldehyde is any one of 6:1, 8:1, 10:1, 12:1, 14:1, 16:1, 18:1, 20:1, etc.
[0017] As an optional implementation, in the step (2), the molar ratio of the intermediate compound I to the sodium tert-pentoxide is 1:(1.1-1.5); for example, the molar ratio of the intermediate compound I to the sodium tert-pentoxide is any one of 1:1.1, 1:1.2, 1:1.3, 1:1.4, 1:1.5.
[0018] As an optional implementation, in the step (2), the ratio of the intermediate compound I to the sodium tert-pentoxide is (0.1-2):1, preferably 1:1, in the unit of g:ml; As an optional implementation, in the step (2), the temperature of the substitution reaction is 100-120℃, and the reaction time is 4-12h; As an optional implementation, in the step (2), the reaction solvent further includes N,N-dimethylformamide; preferably, the ratio of the intermediate compound I to the N,N-dimethylformamide is 1:(2-8), preferably 1:3, in the unit of g:ml; As an optional implementation, the temperature of the hydrolysis reaction is -5℃ to 25℃, preferably 0℃; the time of the hydrolysis reaction is 0.5h to 3h, preferably 1h. For example, the temperature of the hydrolysis reaction can be any value of -5℃, 0℃, 5℃, 10℃, 15℃, 20℃, 25℃, etc., and the time can be any value of 0.5h, 1h, 2h, 3h, etc.
[0019] As an optional implementation, step (2) further includes at least one of extraction, washing, and decolorization after the hydrolysis reaction; As an optional implementation, step (2) involves extraction using an extractant comprising methyl tert-butyl ether, wherein the ratio of methyl tert-butyl ether to intermediate compound I is (6-16):1, more preferably 8:1, in ml:g. As an optional implementation, in step (2), water is used for washing, and the ratio of water to intermediate compound I is (8-18):1, more preferably 8:1, in ml:g; As an optional implementation, step (2) involves using a decolorizing agent and a decolorizing solvent for decolorization; Preferably, the decolorizing agent comprises activated clay, and the mass ratio of the activated clay to the intermediate compound I is (0.05-0.4):1, more preferably 0.1:1; Preferably, the decolorizing solvent comprises n-heptane, and the ratio of n-heptane to intermediate compound I is (5-12):1, more preferably 6:1, in ml:g.
[0020] As an optional implementation, step (3) specifically includes: reacting methyltriphenylphosphine bromide and potassium tert-butoxide in a reaction solvent to generate a phosphorus ylide reagent, and then reacting it with the intermediate compound II to prepare p-tert-pentoxystyrene.
[0021] As an optional implementation, the molar ratio of the intermediate compound II to the methyltriphenylphosphine bromide is 1:(1.2-1.4); As an optional implementation, the molar ratio of intermediate compound II to potassium tert-butoxide is 1:(1.25-1.5); As an optional implementation, in step (3), the reaction solvent includes tetrahydrofuran. Preferably, the volume ratio of intermediate compound II to tetrahydrofuran is 1:(5-10), and more preferably 1:6.
[0022] As an optional implementation, step (3) further includes at least one of the following steps: quenching, extraction, washing, pulping, vacuum filtration, and purification; Preferably, water is used for the quenching, and the volume ratio of water to intermediate compound II is (3-10):1, more preferably 5:1; Preferably, methyl tert-butyl ether is used for the extraction, and the volume ratio of methyl tert-butyl ether to intermediate compound II is (10-20):1, more preferably 10:1; Preferably, water is used for the washing, and the volume ratio of water to intermediate compound II is (3-10):1, more preferably 4:1; Preferably, n-heptane is used for pulping, and the volume ratio of n-heptane to intermediate compound II is (6-20):1, more preferably 8:1; Preferably, the purification is performed using vacuum distillation.
[0023] A second aspect of the present invention provides a p-tert-pentyloxystyrene prepared by the above-described preparation method.
[0024] The third aspect of this invention provides an application of the p-tert-pentoxystyrene prepared by the above-described method in polymer synthesis, electronic materials, daily chemical fragrances, or pharmaceutical research and development.
[0025] The technical solution provided by the embodiments of the present invention has the following advantages compared with the prior art: 1. The present invention provides a method for preparing p-tert-pentyloxystyrene, which includes (1) condensing alcohols and / or esters with 4-fluorobenzaldehyde to prepare intermediate compound I; (2) subjecting intermediate compound I and sodium tert-pentyl alcohol to a substitution reaction in a reaction solvent, and then preparing intermediate compound II by hydrolysis after the reaction; the reaction solvent includes tert-pentyl alcohol; (3) subjecting intermediate compound II to a Wittig reaction to prepare p-tert-pentyloxystyrene. This preparation method has the advantages of simple and easy-to-control synthesis steps, high efficiency, convenience, readily available raw materials, high yield of intermediates and products, high product purity, and easy purification. The p-tert-pentyloxystyrene obtained has an irreplaceable role in polymer synthesis, electronic materials, daily chemical fragrances and pharmaceutical research and development, and shows good application prospects, especially in the fields of high-performance polymers and microelectronic materials. The product has broad application prospects. Attached Figure Description
[0026] The accompanying drawings, which are incorporated in and form part of this specification, illustrate embodiments consistent with this application and, together with the description, serve to explain the principles of this application.
[0027] To more clearly illustrate the technical solutions in the embodiments of this application or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, for those skilled in the art, other drawings can be obtained based on these drawings without creative effort.
[0028] Figure 1 The intermediate compound I synthesized in Example 1 of this invention 1 HNMR spectrum; Figure 2 It is the intermediate compound II synthesized in Example 1 of this invention. 1 HNMR spectrum; Figure 3 This is the p-tert-pentoxystyrene synthesized in Example 1 of this invention. 1 HNMR spectrum; Figure 4 This is the HPLC spectrum of p-tert-pentoxystyrene synthesized in Example 1 of this invention. Detailed Implementation
[0029] To better understand the above-mentioned objectives, features, and advantages of this application, the solution of this application will be further described below. It should be noted that, unless otherwise specified, the embodiments and features described in these embodiments can be combined with each other.
[0030] Many specific details are set forth in the following description in order to provide a full understanding of this application, but this application may also be implemented in other ways different from those described herein; obviously, the embodiments in the specification are only some embodiments of this application, and not all embodiments.
[0031] To provide a method for preparing p-tert-pentyloxystyrene, the present invention provides the following technical solution, wherein the method for preparing p-tert-pentyloxystyrene includes the following steps: (1) Using p-toluenesulfonic acid (TsOH) as a catalyst and toluene (Tol) as a reaction solvent, alcohols and / or esters are subjected to aldol condensation reaction with 4-fluorobenzaldehyde (SM1). After quenching, extraction, washing, pulping, vacuum filtration and drying, intermediate compound I is prepared. (2) Intermediate compound I and sodium tert-amyl alcohol undergo a substitution reaction in a reaction solvent, which includes tert-amyl alcohol and DMF. After the reaction is completed, the temperature is lowered and a hydrolysis reaction is carried out under acidic conditions. After extraction, washing, and decolorization, intermediate compound II is prepared. An acid solution is added to make the reaction system acidic. The concentration of the acid solution is 0.1-5 M, preferably 0.5 M. The acid solution includes hydrochloric acid, trifluoroacetic acid, sulfuric acid or acetic acid, and some Lewis acids. (3) Under nitrogen protection, methyltriphenylphosphine bromide (MePPh3Br), potassium tert-butoxide (t-BuOK) and reaction solvent are reacted at 0-60℃ (e.g., room temperature) to generate phosphorus ylide reagent. Then, a tetrahydrofuran solution containing intermediate compound II is slowly added and the reaction is carried out for 1-5 hours. After quenching, extraction, washing, pulping, vacuum filtration and purification, p-tert-pentoxystyrene is prepared.
[0032] The reaction process is as follows:
[0033] Example 1 This embodiment provides a method for preparing p-tert-pentoxystyrene, including the following steps: (1) Toluene (500 mL, 5.0 V) was added to a 1 L four-necked jacketed reaction flask equipped with a stirrer, water separator, condenser and thermometer, and stirring was started. At room temperature, raw material SM1 (100 g, 0.81 mol, 1.0 eq.), p-toluenesulfonic acid (6.9 g, 0.04 mol, 0.05 eq.) and ethylene glycol (60.0 g, 0.97 mol, 1.2 eq.) were added to the reaction flask. The temperature was slowly raised to 110 °C and kept at this temperature for 5 h. The reaction was monitored by HPLC. After the reaction was completed, the reaction solution was cooled to 20 °C and then quenched in 500 mL of 1% wt sodium bisulfite aqueous solution. The solution was stirred for 15 min and allowed to stand before separation to obtain the organic phase and aqueous phase. The aqueous phase was extracted once with 400 mL of toluene. The organic phases were combined and washed once with 400 mL of water. The organic phase was concentrated at 80 °C. The crude product after concentration was extracted with 800 mL of toluene. Dissolved in mL of n-heptane and slurried, stirred at 10 °C for 1 h, then filtered under reduced pressure. The filter cake was collected, dried, and 128 g of white solid product compound was obtained, which is intermediate compound I. HPLC analysis showed a purity of 99.4% and a yield of 94.5%. ¹H NMR (400 MHz, Chloroform- d ) δ 7.53 – 7.44 (m, 2H), 7.37 – 7.30 (m, 2H), 5.74 (s, 1H), 4.11 – 3.95 (m, 4H), see Figure 1 .
[0034] (2) Under nitrogen protection, DMF (150 mL, 3.0 V) and tert-amyl alcohol (50 mL, 1.0 V) were added to a 1 L four-necked jacketed reaction flask equipped with a stirrer, condenser, and thermometer, and stirring was started. At room temperature, intermediate compound I (50 g, 0.3 mol, 1.0 eq.) was added to the reaction flask, followed by sodium tert-amyl alcohol (39.3 g, 0.36 mol, 1.2 eq.). The reaction solution was slowly heated to 120 °C and kept at this temperature for 4 h. The reaction was monitored by HPLC. After the reaction was completed, the reaction solution was cooled to 0 °C, and 200 mL of 0.5 mol / L hydrochloric acid aqueous solution was slowly added to the reaction flask. The mixture was kept at this temperature and stirred for 1 h. The reaction was carried out by hydrolysis. Methyl tert-butyl ether was extracted twice, with 200 ml used each time. The organic phases were combined and washed twice with 200 ml of water each time. The mixture was concentrated under reduced pressure at 40°C to remove methyl tert-butyl ether, yielding a crude product. The crude product was dissolved in 300 mL of n-heptane with stirring, and then 5 g of activated clay was added. After stirring for 30 min, the mixture was filtered and concentrated under reduced pressure at 50°C to remove n-heptane, yielding 56.1 g of a light yellow liquid intermediate, namely intermediate compound II. The purity was determined by GC to be 98.5%, and the yield was 98.1%. 1 H NMR (400 MHz, DMSO-d6) δ 9.89 (s, 1H), 7.86–7.80 (m, 2H), 7.19–7.13 (m,2H), 1.74 (q, J=7.5 Hz, 2H), 1.35 (s, 6H), 0.93 (t, J=7.5 Hz, 3H), see Figure 2 .
[0035] (3) Under nitrogen protection, tetrahydrofuran (200 mL, 4.0 V) was added to a 0.5 L four-necked jacketed reaction flask equipped with a stirrer, condenser, and thermometer, and stirring was started. At 25°C, MePPh3Br (111.5 g, 0.31 mol, 1.2 eq.) was first added to the reaction flask, followed by the slow addition of potassium tert-butoxide (36.5 g, 0.33 mol, 1.27 eq.). The reaction was maintained at this temperature for 1 h. Finally, a tetrahydrofuran solution (100 mL, 2.0 V) of intermediate compound II (50 g, 0.26 mol, 1.0 eq.) was added dropwise. After the addition was complete, the reaction was maintained at this temperature for 3 h. The reaction was monitored by HPLC. After the reaction was complete, the reaction solution was slowly quenched in 250 mL of water, and then extracted twice with methyl tert-butyl ether (MTBE), with each extraction using 250 mL of MTBE. The organic phases were combined and 200 mL of water was used for extraction. Wash once with mL of water, concentrate under reduced pressure at 40℃ until the solvent is no longer present, add 400 mL of n-heptane to dissolve and slurry, stir at 0℃ for 1 h, filter, collect the filtrate, add 200 ppm of p-tert-butylcatechol as a polymerization inhibitor to the filtrate, concentrate under reduced pressure at 60℃, and concentrate to dryness to obtain a colorless or light yellow liquid crude product. The crude product is purified by reduced pressure distillation (vacuum degree -101 Kpa, oil bath temperature 105℃) to obtain a colorless transparent product p-tert-pentoxystyrene, 43.5 g, with a purity of 99.78% as determined by HPLC. The HPLC chromatogram is shown in [Figure number missing]. Figure 4 The yield was 87.9%. 1 H NMR (400 MHz, Chloroform-d)δ7.37–7.26 (m, 2H),7.00–6.87 (m, 2H), 6.67 (dd, J=17.6, 10.9 Hz, 1H), 5.64 (dd, J=17.6, 1.0 Hz,1H), 5.16 (dd, J=10.9, 1.0 Hz, 1H), 1.68 (q, J=7.5 Hz, 2H), 1.27 (s, 6H), 1.01 (t, J=7.5 Hz, 3H), see Figure 3 .
[0036] Examples 2-8 Examples 2-8 provide a method for preparing p-tert-pentoxystyrene, which is basically the same as that in Example 1. The main difference is that the parameters of the raw materials and the reaction conditions in step (1) are different. The main differences are shown in Table 1.
[0037] NMR verification confirmed that intermediate compound I, intermediate compound II, and p-tert-pentoxystyrene were prepared in all of Examples 2-8.
[0038] Table 1 Main differences in step (1)
[0039] Note: The mass of SM1 in the starting material of each example is 100g; the purity and yield in Table 1 refer to the purity and yield of intermediate compound I.
[0040] Examples 9-15 Examples 9-15 provide a method for preparing p-tert-pentoxystyrene, which is basically the same as that in Example 1. The main difference is that the parameters of the raw materials and the reaction conditions in step (2) are different. The main differences are shown in Table 2.
[0041] NMR verification showed that intermediate compound I, intermediate compound II, and p-tert-pentoxystyrene could all be prepared in Examples 9-15.
[0042] Table 2 Main differences in step (2)
[0043] Note: The mass of intermediate compound I in each example is 50g; the purity and yield in Table 2 refer to the purity and yield of intermediate compound II.
[0044] Examples 16-23 Examples 16-23 provide a method for preparing p-tert-pentoxystyrene, which is basically the same as that in Example 1. The main difference is that the parameters of the raw materials and the reaction conditions in step (3) are different. The main differences are shown in Table 3.
[0045] NMR verification confirmed that intermediate compound I, intermediate compound II, and p-tert-pentoxystyrene could all be prepared in Examples 16-23.
[0046] Table 3 Main differences in step (3)
[0047] Note: The mass of intermediate compound II in each example is 50g; purity and yield refer to the purity and yield of p-tert-pentoxystyrene.
[0048] As can be seen from Tables 1-3, in the preparation of p-tert-pentoxystyrene by the method of the present invention, the intermediate compound I obtained in step (1) has a purity >99.1%, a stable yield of over 90%, stable product quality, high yield, and is easy to operate without the need for column chromatography purification. The intermediate compound II obtained in step (2) has a purity between 98.0% and 98.7%, a stable yield of over 97.3%, stable product quality, high yield, and is easy to operate. The crude product can be directly used in the next reaction without further purification, especially when the substitution reaction temperature is 100-120℃, which can further improve the yield of intermediate compound II. The p-tert-pentoxystyrene prepared by the present invention has a purity of over 99.70%, a stable yield of around 88%, stable product quality, and is easy to purify.
[0049] It should be noted that, in this document, relational terms such as "first" and "second" are used merely to distinguish one entity or operation from another, and do not necessarily require or imply any such actual relationship or order between these entities or operations. Furthermore, the terms "comprising," "including," or any other variations thereof are intended to cover non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements includes not only those elements but also other elements not expressly listed, or elements inherent to such a process, method, article, or apparatus. Without further limitations, an element defined by the phrase "comprising one..." does not exclude the presence of other identical elements in the process, method, article, or apparatus that includes said element.
[0050] The above description is merely a specific embodiment of this application, enabling those skilled in the art to understand or implement this application. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of this application. Therefore, this application is not to be limited to the embodiments described herein, but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims
1. A process for the preparation of p-tert-butoxy-styrene, characterized in that, The method comprises the following steps: (1) an alcohol and / or an ester is subjected to a condensation reaction with 4-fluorobenzaldehyde to prepare an intermediate compound I; (2) the intermediate compound I and sodium tert-pentoxide are subjected to a substitution reaction in a reaction solvent, and after the reaction is completed, the intermediate compound II is prepared through a hydrolysis reaction; the reaction solvent comprises tert-pentanol; (3) the intermediate compound II is subjected to a wittig reaction to prepare p-tert-butoxy styrene.
2. The production method according to claim 1, characterized by, The molar ratio of the alcohol and / or the ester to the 4-fluorobenzaldehyde is (1.1-1.5):1; Preferably, the alcohol comprises at least one of methanol, ethanol, n-propanol, isopropanol or n-butanol; and the dihydric alcohol comprises at least one of ethylene glycol, propylene glycol or butylene glycol; Preferably, the ester comprises at least one of trimethyl orthoformate, triethyl orthoformate or tripropyl orthoformate; Preferably, the condensation reaction is carried out at a temperature of 80-120 DEG C for 3-8 hours; Preferably, the condensation reaction uses p-toluenesulfonic acid as a catalyst; and the molar ratio of the 4-fluorobenzaldehyde to the p-toluenesulfonic acid is 1:(0.03-0.2); Preferably, the condensation reaction uses toluene as a reaction solvent; and the volume ratio of the 4-fluorobenzaldehyde to the toluene is 1:(2-8), preferably 1:
5.
3. The production method according to claim 1 or 2, characterized by, After the condensation reaction, the step (1) further comprises at least one of quenching, extraction, washing, beating and reduced-pressure filtration; Preferably, the quenching is carried out using a quenching agent, and the quenching agent comprises an aqueous sodium bisulfite solution; Preferably, the volume ratio of the aqueous sodium bisulfite solution to the 4-fluorobenzaldehyde is (4-10):1, preferably 5:1, and the concentration of the aqueous sodium bisulfite solution is 1wt%; Preferably, the extraction is carried out using an extraction agent, and the extraction agent comprises toluene; and the volume ratio of the toluene to the 4-fluorobenzaldehyde is (4-10):1, preferably 4:1; Preferably, the washing is carried out using a washing agent, and the washing agent comprises water; and the volume ratio of the water to the 4-fluorobenzaldehyde is (3-10):1, preferably 4:1; Preferably, the beating is carried out using n-heptane; and the volume ratio of the n-heptane to the 4-fluorobenzaldehyde is (6-20):1, preferably 8:
1.
4. The production method according to any one of claims 1 to 3, characterized by, The molar ratio of the intermediate compound I to the sodium tert-pentoxide is 1:(1.1-1.5); Preferably, the ratio of the intermediate compound I to the tert-pentanol is (0.1-2):1, preferably 1:1, in units of g:ml; Preferably, the substitution reaction is carried out at a temperature of 100-120 DEG C for 4-12 hours; Preferably, the reaction solvent further comprises N,N-dimethylformamide; and the ratio of the intermediate compound I to N,N-dimethylformamide is 1:(2-8), preferably 1:3, in units of g:ml; And / or, the temperature of the hydrolysis reaction is -5℃-25℃, preferably 0℃; the time of the hydrolysis reaction is 0.5h-3h, preferably 1h.
5. The production method according to any one of claims 1 to 4, characterized by, The step (2) further comprises at least one of extraction, washing, decolorization after the hydrolysis reaction; Preferably, the extraction is carried out by using an extraction agent, the extraction agent comprises methyl tert-butyl ether, the ratio of the methyl tert-butyl ether to the intermediate compound I is (6-16):1, more preferably 8:1, unit: ml:g; Preferably, the washing is carried out by using water, the ratio of the water to the intermediate compound I is (8-18):1, more preferably 8:1, unit: ml:g; Preferably, the decolorization is carried out by using a decolorization reagent and a decolorization solvent; Preferably, the decolorization reagent comprises activated clay, the mass ratio of the activated clay to the intermediate compound I is (0.05-0.4):1, more preferably 0.1:1; Preferably, the decolorization solvent comprises n-heptane, the ratio of the n-heptane to the intermediate compound I is (5-12):1, more preferably 6:1, unit: ml:g.
6. The method of any one of claims 1-5, wherein, The step (3) specifically comprises: methyltriphenylphosphonium bromide and potassium tert-butoxide are reacted in a reaction solvent to generate a phosphorus ylide reagent, and then the phosphorus ylide reagent is reacted with the intermediate compound II to prepare p-tert-butoxy styrene.
7. The production method according to claim 6, wherein The molar ratio of the intermediate compound II to the methyltriphenylphosphonium bromide is 1:(1.2-1.4); And / or, the molar ratio of the intermediate compound II to the potassium tert-butoxide is 1:(1.25-1.5); And / or, in the step (3), the reaction solvent comprises tetrahydrofuran, preferably, the volume ratio of the intermediate compound II to the tetrahydrofuran is 1:(5-10), preferably 1:
6.
8. The preparation method according to claim 6, characterized in that, Further comprising at least one of quenching, extraction, washing, beating, reduced pressure filtration and purification; Preferably, the quenching is carried out by using water, the volume ratio of the water to the intermediate compound II is (3-10):1, more preferably 5:1; Preferably, the extraction is carried out by using methyl tert-butyl ether, the volume ratio of the methyl tert-butyl ether to the intermediate compound II is (10-20):1, more preferably 10:1; Preferably, the washing is carried out by using water, the volume ratio of the water to the intermediate compound II is (3-10):1, more preferably 4:1; Preferably, the beating is carried out by using n-heptane, the volume ratio of the n-heptane to the intermediate compound II is (6-20):1, more preferably 8:1; Preferably, the purification is carried out by using reduced pressure distillation.
9. The application of p-tert-butoxy styrene prepared by the preparation method in any one of claims 1-8 in the research and development of high polymer synthesis, electronic materials, daily chemical perfumes or medicines.