CN113149875A - Method for preparing p-methylsulfonylbenzaldehyde by continuous flow - Google Patents
Method for preparing p-methylsulfonylbenzaldehyde by continuous flow Download PDFInfo
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- CN113149875A CN113149875A CN202110459106.8A CN202110459106A CN113149875A CN 113149875 A CN113149875 A CN 113149875A CN 202110459106 A CN202110459106 A CN 202110459106A CN 113149875 A CN113149875 A CN 113149875A
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- methylsulfonylbenzaldehyde
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- PSVPUHBSBYJSMQ-UHFFFAOYSA-N 4-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=C(C=O)C=C1 PSVPUHBSBYJSMQ-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 230000007062 hydrolysis Effects 0.000 claims abstract description 24
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 24
- JRRKYOFPKIKWOL-UHFFFAOYSA-N 1-(dibromomethyl)-4-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=C(C=C1)C(Br)Br JRRKYOFPKIKWOL-UHFFFAOYSA-N 0.000 claims abstract description 21
- YYDNBUBMBZRNQQ-UHFFFAOYSA-N 1-methyl-4-methylsulfonylbenzene Chemical compound CC1=CC=C(S(C)(=O)=O)C=C1 YYDNBUBMBZRNQQ-UHFFFAOYSA-N 0.000 claims abstract description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000000926 separation method Methods 0.000 claims abstract description 7
- 238000000746 purification Methods 0.000 claims abstract description 4
- 238000005893 bromination reaction Methods 0.000 claims description 89
- 230000031709 bromination Effects 0.000 claims description 88
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- 239000003513 alkali Substances 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 6
- 238000005086 pumping Methods 0.000 claims description 6
- 238000005112 continuous flow technique Methods 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 5
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- AYIRNRDRBQJXIF-NXEZZACHSA-N (-)-Florfenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl)C=C1 AYIRNRDRBQJXIF-NXEZZACHSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229960003760 florfenicol Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BEARMXYKACECDH-UHFFFAOYSA-N methylsulfonylmethylbenzene Chemical compound CS(=O)(=O)CC1=CC=CC=C1 BEARMXYKACECDH-UHFFFAOYSA-N 0.000 description 2
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- QRVYABWJVXXOTN-UHFFFAOYSA-N 4-methylsulfanylbenzaldehyde Chemical compound CSC1=CC=C(C=O)C=C1 QRVYABWJVXXOTN-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940124350 antibacterial drug Drugs 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/06—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing p-methylsulfonylbenzaldehyde by continuous flow, which takes molten p-methylsulfonyl toluene and liquid bromine as raw materials, and the raw materials are continuously conveyed into a reactor with six kettles connected in series for reaction to obtain p-methylsulfonyl dibromotoluene; the p-methylsulfonyl dibromotoluene is subjected to hydrolysis, separation, purification and other steps in sequence to obtain high-purity p-methylsulfonyl benzaldehyde. The method has the advantages of high safety, small environmental pollution, simple operation, high automation degree and the like, the purity of the prepared product can reach more than 99 percent, and the method has good application value and industrialization prospect.
Description
Technical Field
The invention relates to the technical field of chemical pharmacy, in particular to a method for preparing p-methylsulfonylbenzaldehyde by continuous flow.
Background
The p-methylsulfonylbenzaldehyde is an important medical intermediate of florfenicol and the like, the florfenicol is a novel veterinary special chloramphenicol broad-spectrum antibacterial drug, the drug is approved to be on the market in Japan, France, England and other countries in the 90 th century, and China also has approved the drug to be on the market. In addition, p-methylsulfonylbenzaldehyde can be used as an important intermediate for human antibiotics and pesticides.
In the prior art, methylsulfonyl toluene can be used as a raw material to prepare p-methylsulfonyl benzaldehyde, for example, chinese patent CN102827041B discloses a method for preparing p-methyl mock benzaldehyde, which is a method for preparing p-methylsulfonyl dibromotoluene by bromination reaction of methylsulfonyl toluene and bromine at high temperature, and then hydrolysis to obtain p-methylsulfonyl benzaldehyde. The method is an intermittent reaction, the labor intensity is high, a large amount of bromine is accumulated in the reaction process, and the danger degree is high.
Chinese patent CN110903225A discloses a method for synthesizing p-methyl alum benzaldehyde, which takes sodium methyl mercaptide and p-chlorobenzaldehyde as raw materials, reacts under the action of a phase transfer catalyst to generate p-methyl mercapto benzaldehyde, and then the p-methyl sulfone benzaldehyde is prepared by the method of oxidizing by peroxyacetic acid aqueous solution. Although the reaction conditions are mild, sodium methyl mercaptide has foul smell and is not environment-friendly, and peracetic acid is extremely unstable and has explosion risks in the use and storage processes.
Disclosure of Invention
The invention aims to provide a method for continuously preparing p-methylsulfonylbenzaldehyde by flow, aiming at the defects in the prior art.
In order to achieve the purpose, the invention adopts the following technical scheme:
a continuous flow process for preparing p-methylsulfonylbenzaldehyde, comprising the steps of:
(1) bromination: pumping the molten p-methylsulfonyl toluene into a first-stage bromination kettle, entering a second-stage bromination kettle in an overflow mode through a first-stage bromination kettle side outlet, entering a third-stage bromination kettle in an overflow mode through a second-stage bromination kettle side outlet, entering a fourth-stage bromination kettle in an overflow mode through a third-stage bromination kettle side outlet, entering a fifth-stage bromination kettle in an overflow mode through a fourth-stage bromination kettle side outlet, entering a sixth-stage bromination kettle in an overflow mode through a fifth-stage bromination kettle side outlet, and entering a hydrolysis kettle through a sixth-stage bromination kettle discharge port; liquid bromine enters from one or more stages of reaction kettles from one to six stages of reaction kettles, and contacts and reacts with p-methylsulfonyl toluene through a submerged extension tube to obtain p-methylsulfonyl dibromotoluene;
(2) hydrolysis: hydrolyzing the p-methylsulfonyl dibromotoluene obtained in the step (1) in a hydrolysis kettle at the hydrolysis temperature of 20-100 ℃ for 0.5-20 h;
(3) separation: sequentially crystallizing and centrifuging the solution hydrolyzed in the step (2) to obtain a p-methylsulfonylbenzaldehyde crude product;
(4) and (3) purification: adding alkali liquor into the p-methylsulfonylbenzaldehyde crude product obtained in the step (3) for washing, and then centrifuging to obtain a p-methylsulfonylbenzaldehyde fine product; the temperature of the alkali liquor is 5-100 ℃.
In the invention, the method for preparing the p-methylsulfonyl dibromotoluene by adopting continuous flow can ensure that the liquid bromine is fully contacted with the p-methylsulfonyl toluene, thereby improving the reaction rate. Compared with the batch reaction, the yield of the p-methylsulfonyl dibromotoluene is obviously improved, the liquid bromine consumption is obviously reduced, and the whole reaction process is safe and efficient.
Preferably, the reaction temperature of the first-stage to sixth-stage reaction kettle is 100-200 ℃.
Preferably, the temperature of the molten p-methylsulfonyltoluene in the step (1) is 87-200 ℃.
Preferably, the mass ratio of the p-methylsulfonyl dibromotoluene to the water in the step (2) is 1: 1-50.
Preferably, the alkali solution in step (4) is one or more of sodium carbonate, sodium bicarbonate and sodium hydroxide.
Preferably, the pH value of the alkali liquor is 7-14.
Compared with the prior art, the invention has the following advantages and beneficial effects:
in the invention, the molten p-methylsulfonyl toluene and liquid bromine continuously enter a reaction system, so that the accumulation amount of materials in a reaction kettle is obviously reduced, and the reaction is safe and efficient; the batch reaction is changed into continuous reaction, and the labor intensity can be obviously reduced.
The preparation method has high safety, high product purity of over 99 percent, small environmental pollution and high equipment automation degree, is suitable for industrial large-scale production, and has good application value.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The test methods or test methods described in the following examples are conventional methods unless otherwise specified; the reagents and materials, unless otherwise indicated, are conventionally obtained commercially or prepared by conventional methods.
The invention provides a continuous flow preparation method of p-methylsulfonylbenzaldehyde, which comprises the following steps:
(1) bromination: pumping the molten p-methylsulfonyl toluene into a first-stage bromination kettle, entering a second-stage bromination kettle in an overflow mode through a first-stage bromination kettle side outlet, entering a third-stage bromination kettle in an overflow mode through a second-stage bromination kettle side outlet, entering a fourth-stage bromination kettle in an overflow mode through a third-stage bromination kettle side outlet, entering a fifth-stage bromination kettle in an overflow mode through a fourth-stage bromination kettle side outlet, entering a sixth-stage bromination kettle in an overflow mode through a fifth-stage bromination kettle side outlet, and entering a hydrolysis kettle through a sixth-stage bromination kettle discharge port; liquid bromine enters from one or more stages of reaction kettles from one to six stages of reaction kettles, and contacts and reacts with p-methylsulfonyl toluene through a submerged extension tube to obtain p-methylsulfonyl dibromotoluene;
(2) hydrolysis: hydrolyzing the p-methylsulfonyl dibromotoluene obtained in the step (1) in a hydrolysis kettle at the hydrolysis temperature of 20-100 ℃ for 0.5-20 h;
(3) separation: sequentially crystallizing and centrifuging the solution hydrolyzed in the step (2) to obtain a p-methylsulfonylbenzaldehyde crude product;
(4) and (3) purification: adding alkali liquor into the p-methylsulfonylbenzaldehyde crude product obtained in the step (3) for washing, and then centrifuging to obtain a p-methylsulfonylbenzaldehyde fine product; the temperature of the alkali liquor is 5-100 ℃.
The reaction temperature of the first-stage to sixth-stage reaction kettle is 100-200 ℃.
The temperature for melting the p-methylsulfonyl toluene in the step (1) is 87-200 ℃.
In the step (2), the mass ratio of the p-methylsulfonyl dibromotoluene to the water is 1: 1-50.
The alkali liquor in the step (4) is one or more of sodium carbonate, sodium bicarbonate and sodium hydroxide.
The pH value of the alkali liquor is 7-14.
Example 1
This example provides a continuous flow process for the preparation of p-methylsulfonylbenzaldehyde, comprising the following steps:
bromination in step (1): keeping the reaction temperature of the first-fifth-stage bromination kettle at 120 ℃ and the reaction temperature of the sixth-stage bromination kettle at 155 ℃, pumping 100 ℃ p-methylsulfonyl toluene into the first-stage bromination kettle, entering the second-stage bromination kettle in an overflow mode through a side outlet of the first-stage bromination kettle, entering the third-stage bromination kettle in an overflow mode through a side outlet of the second-stage bromination kettle, entering the fourth-stage bromination kettle in an overflow mode through a side outlet of the third-stage bromination kettle, entering the fifth-stage bromination kettle in an overflow mode through a side outlet of the fourth-stage bromination kettle, entering the sixth-stage bromination kettle in an overflow mode through a side outlet of the fifth-stage bromination kettle, and entering the hydrolysis kettle through a discharge port of the sixth-stage bromination kettle; on the other hand, liquid bromine enters from the first-stage bromination kettle, passes through the submerged extension tube, and contacts and reacts with the p-methylsulfonyl toluene to obtain the p-methylsulfonyl dibromotoluene.
Step (2) hydrolysis: hydrolyzing the p-methylsulfonyl dibromotoluene obtained in the step (1) in a hydrolysis kettle at the temperature of 90 ℃ for 2h to obtain a product solution.
And (3) separation: and (3) crystallizing and centrifuging the product solution obtained in the step (2) in sequence to obtain a p-methylsulfonylbenzaldehyde crude product.
And (4) purifying: and (4) adding the p-methylsulfonylbenzaldehyde crude product obtained in the step (3) into a sodium hydroxide solution with the temperature of 25 ℃ and the pH value of 11, washing, and centrifuging to obtain the p-methylsulfonylbenzaldehyde with the purity of 99.8%.
Example 2
This example provides a continuous flow process for the preparation of p-methylsulfonylbenzaldehyde, comprising the following steps:
bromination in step (1): keeping the reaction temperature of a first-stage bromination kettle to a sixth-stage bromination kettle at 200 ℃, pumping 120 ℃ p-methylsulfonyl toluene into the first-stage bromination kettle, entering the second-stage bromination kettle in an overflow mode through a side outlet of the first-stage bromination kettle, entering the third-stage bromination kettle in an overflow mode through a side outlet of the second-stage bromination kettle, entering the fourth-stage bromination kettle in an overflow mode through a side outlet of the third-stage bromination kettle, entering the fifth-stage bromination kettle in an overflow mode through a side outlet of the fourth-stage bromination kettle, entering the sixth-stage bromination kettle in an overflow mode through a side outlet of the fifth-stage bromination kettle, and entering a hydrolysis kettle through a discharge port of the sixth-stage bromination kettle; on the other hand, liquid bromine enters from the second-stage bromination kettle and the fourth-stage bromination kettle, passes through the submerged extension tube, and contacts and reacts with the p-methylsulfonyl toluene to obtain the p-methylsulfonyl dibromotoluene.
Step (2) hydrolysis: hydrolyzing the p-methylsulfonyl dibromotoluene obtained in the step (1) in a hydrolysis kettle at 100 ℃ for 7h to obtain a product solution.
And (3) separation: and (3) crystallizing and centrifuging the product solution obtained in the step (2) in sequence to obtain a p-methylsulfonylbenzaldehyde crude product.
And (4) purifying: and (4) adding the p-methylsulfonylbenzaldehyde crude product obtained in the step (3) into a sodium carbonate solution with the temperature of 60 ℃ and the pH value of 8, washing, and centrifuging to obtain the p-methylsulfonylbenzaldehyde with the purity of 99.1%.
Example 3
This example provides a continuous flow process for the preparation of p-methylsulfonylbenzaldehyde, comprising the following steps:
bromination in step (1): keeping the reaction temperature of the first to fourth-stage bromination kettles at 170 ℃ and the temperature of the fifth to sixth-stage bromination kettles at 190 ℃, pumping 150 ℃ p-methylsulfonyl toluene into the first-stage bromination kettle, entering the second-stage bromination kettle in an overflow manner through a side outlet of the first-stage bromination kettle, entering the third-stage bromination kettle in an overflow manner through a side outlet of the second-stage bromination kettle, entering the fourth-stage bromination kettle in an overflow manner through a side outlet of the third-stage bromination kettle, entering the fifth-stage bromination kettle in an overflow manner through a side outlet of the fourth-stage bromination kettle, entering the sixth-stage bromination kettle in an overflow manner through a side outlet of the fifth-stage bromination kettle, and entering the hydrolysis kettle through a discharge port of the sixth-stage bromination kettle; on the other hand, liquid bromine enters from the first to fifth-stage bromination kettles, passes through the submerged extension tube, and contacts and reacts with the p-methylsulfonyl toluene to obtain the p-methylsulfonyl dibromotoluene.
Step (2) hydrolysis: hydrolyzing the p-methylsulfonyl dibromotoluene obtained in the step (1) in a hydrolysis kettle at 60 ℃ for 16h to obtain a product solution.
And (3) separation: and (3) crystallizing and centrifuging the product solution obtained in the step (2) in sequence to obtain a p-methylsulfonylbenzaldehyde crude product.
And (4) purifying: and (4) adding the p-methylsulfonylbenzaldehyde crude product obtained in the step (3) into a sodium hydroxide solution with the temperature of 80 ℃ and the pH value of 14 for washing, and centrifuging to obtain the p-methylsulfonylbenzaldehyde with the purity of 99.9%.
In conclusion, the invention takes the molten p-methylsulfonyl toluene and liquid bromine as raw materials, p-methylsulfonyl dibromotoluene is synthesized by a multi-kettle series connection mode, and the p-methylsulfonyl benzaldehyde with the purity of over 99 percent can be obtained by the steps of hydrolysis, alkali washing and the like.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (6)
1. A continuous flow process for the preparation of p-methylsulfonylbenzaldehyde, which comprises the steps of:
(1) bromination: pumping the molten p-methylsulfonyl toluene into a first-stage bromination kettle, entering a second-stage bromination kettle in an overflow mode through a first-stage bromination kettle side outlet, entering a third-stage bromination kettle in an overflow mode through a second-stage bromination kettle side outlet, entering a fourth-stage bromination kettle in an overflow mode through a third-stage bromination kettle side outlet, entering a fifth-stage bromination kettle in an overflow mode through a fourth-stage bromination kettle side outlet, entering a sixth-stage bromination kettle in an overflow mode through a fifth-stage bromination kettle side outlet, and entering a hydrolysis kettle through a sixth-stage bromination kettle discharge port; liquid bromine enters from one or more stages of reaction kettles from one to six stages of reaction kettles, and contacts and reacts with p-methylsulfonyl toluene through a submerged extension tube to obtain p-methylsulfonyl dibromotoluene;
(2) hydrolysis: hydrolyzing the p-methylsulfonyl dibromotoluene obtained in the step (1) in a hydrolysis kettle at the hydrolysis temperature of 20-100 ℃ for 0.5-20 h;
(3) separation: sequentially crystallizing and centrifuging the solution hydrolyzed in the step (2) to obtain a p-methylsulfonylbenzaldehyde crude product;
(4) and (3) purification: adding alkali liquor into the p-methylsulfonylbenzaldehyde crude product obtained in the step (3) for washing, and then centrifuging to obtain a p-methylsulfonylbenzaldehyde fine product; the temperature of the alkali liquor is 5-100 ℃.
2. The continuous flow method for preparing p-methylsulfonylbenzaldehyde according to claim 1, wherein the reaction temperature of the first to sixth reaction vessels is 100-200 ℃.
3. The continuous flow production method of p-methylsulfonylbenzaldehyde according to claim 1, wherein the temperature of the molten p-methylsulfonyltoluene in step (1) is 87 to 200 ℃.
4. The continuous flow preparation method of p-methylsulfonylbenzaldehyde according to claim 1, wherein the mass ratio of p-methylsulfonyl dibromotoluene to water in step (2) is 1: 1-50.
5. The continuous flow method for preparing p-methylsulfonylbenzaldehyde according to claim 1, wherein the alkali solution in step (4) is one or more of sodium carbonate, sodium bicarbonate and sodium hydroxide.
6. The continuous flow method for preparing p-methylsulfonylbenzaldehyde according to claim 5, wherein the pH of the alkaline solution is 7-14.
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