Preparation method of 4-methylthio benzaldehyde

A technology of benzaldehyde and methylthio group, applied in the field of organic compound synthesis, can solve the problems of unfavorable environment, increased production cost and high reaction temperature, and achieves the effects of reduced production cost, no three waste emissions and high economy.

Inactive Publication Date: 2014-03-05
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] Among the several methods reported above, the raw materials used in the first and second methods are not easy to obtain, and the cost is too high to be suitable for industrial production; in the third method, more expensive p-bromobenzaldehyde is used, and bromine enters as a leaving group. In wastewater, the atomic economy of the reaction is not good, the reaction yield is also low, and the reaction temperature is high, the energy consumption is large, and it is not suitable for industrial production; although the fourth method has simple raw materials, it will produce a large amount of Waste water is not good for the environment, and the cost of waste water treatment increases, which further leads to an increase in production costs; the fifth and sixth methods have too low yields and are not suitable for industrial production

Method used

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  • Preparation method of 4-methylthio benzaldehyde
  • Preparation method of 4-methylthio benzaldehyde
  • Preparation method of 4-methylthio benzaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0042] Embodiment 1, a kind of preparation method of 4-methylthiobenzaldehyde, take thioanisole as raw material, carry out the following steps successively:

[0043] 1) Preparation of SZTA catalyst:

[0044] ①、TiCl 4 and ZrOCl 2 ·8H 2 O mixed to get a mixed solution; ZrOCl 2 ·8H 2 Zr atoms in O and TiCl 4 The ratio of the atomic number of Ti atoms in is 10:1; that is, nZr:nTi=10:1;

[0045] ②. Under rapid stirring (100 rpm), add ammonia water with a concentration of 1mol / L dropwise into the mixed solution obtained in step ① until the pH value is 9, and the resulting reaction system will appear precipitation. The reaction system containing precipitation Aged at room temperature for 24 h; filtered, and the resulting aged precipitate was washed repeatedly until the washing liquid did not contain Cl - until;

[0046] ③. Dry the washed precipitate obtained in step ② at 110°C for 8 hours, cool to room temperature, and grind it into a powder with a particle size of less than...

Embodiment 2

[0050] Embodiment 2, a kind of preparation method of 4-methylthiobenzaldehyde, take thioanisole as raw material, carry out the following steps successively:

[0051] 1) Preparation of SZTA catalyst:

[0052] ①、TiCl 4 and ZrOCl 2 ·8H 2 O mixed to get a mixed solution; ZrOCl 2 ·8H 2 Zr atoms in O and TiCl 4 The ratio of the atomic number of Ti atoms in is 20:1; that is, nZr:nTi=20:1;

[0053] ②. Under rapid stirring (100 rpm), add ammonia water with a concentration of 1 mol / L dropwise to the mixed solution obtained in step ① until the pH value is 9, and the resulting reaction system will appear precipitation. The reaction system containing precipitation is in Aged at room temperature for 24 h; filtered, and the resulting aged precipitate was washed repeatedly until the washing liquid did not contain Cl - until;

[0054] ③. Dry the washed precipitate obtained in step ② at 110°C for 8 hours, cool to room temperature, and grind it into a powder with a particle size of less...

Embodiment 3

[0058] Embodiment 3, a kind of preparation method of 4-methylthiobenzaldehyde, take thioanisole as raw material, carry out the following steps successively:

[0059] 1) Preparation of SZTA catalyst:

[0060] With embodiment 1.

[0061] 2) Weigh 2g of the SZTA catalyst obtained in step 1) and place it in a 50ml stainless steel autoclave lined with polytetrafluoroethylene, add 12ml (0.1mol) thioanisole; the mixture composed of SZTA catalyst and thioanisole After heating to 80°C, feed CO to make the pressure in the autoclave 0.5 MPa, keep warm (80°C) and react for 3 hours. Introduce 50ml of water into the filtrate, stir at 100 rpm for 30min, and the solid obtained is 4-methylthiobenzaldehyde. Finally, 12.2 g of 4-methylthiobenzaldehyde was obtained, and the yield was 80.2%.

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Abstract

The invention discloses a preparation method of 4-methylthio benzaldehyde, comprising the following steps: 1) preparing an SZTA catalyst: mixing TiCl4 and ZrOCl2-8H2O, then adding ammonia water dropwisely to obtain a reaction system containing precipitates, and aging the reaction system containing precipitates, filtering, repeatedly washing the precipitates obtained after aging; after washing, successively putting the precipitates in an ammonium metavanadate solution and (NH4)2SO4 solution for dipping, drying and roasting to obtain an SZTA catalyst; 2) adding the SZTA catalyst and thioanisole in an autoclave to obtain a mixture, heating up the mixture to 70-90 DEG C, then letting CO in to allow the pressure in the autoclave to be 0.5-5 MPa, conducting heat preservation reaction for 3-8h, after completing the reaction, filtering the reaction products, cooling the obtained filtrate to room temperature, and then conducting hydrolysis to obtain 4-methylthio benzaldehyde.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing 4-methylthiobenzaldehyde. Background technique [0002] 4-Methylthiobenzaldehyde, which has the formula C 8 h 8 OS, its structural formula is shown in S-1, its pure product is light yellow crystal, melting point is 267 ° C, it is an important organic intermediate that can be used for the synthesis of dyes and medicine, such as it can be used as a COX-2 inhibitor Rofecoxib and its derivatives, raw materials of intermediates of non-steroidal anti-inflammatory drug lofecoxib, etc., are widely used. [0003] [0004] The method of the synthetic 4-methylthiobenzaldehyde reported in the literature mainly contains following several kinds at present: [0005] 1) Using 4-methylthiobenzyl alcohol as a raw material, 4-methylthiobenzaldehyde is obtained through oxidation, and the yield can reach up to 100% (Chemistry-A European Journal, 2011,17(22...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/22C07C319/20B01J27/053
Inventor 陶明贾银霞周少东钱超陈新志
Owner ZHEJIANG UNIV
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