CN102731352A - Preparation method of 4-methylthio benzaldehyde - Google Patents
Preparation method of 4-methylthio benzaldehyde Download PDFInfo
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- CN102731352A CN102731352A CN2012101933276A CN201210193327A CN102731352A CN 102731352 A CN102731352 A CN 102731352A CN 2012101933276 A CN2012101933276 A CN 2012101933276A CN 201210193327 A CN201210193327 A CN 201210193327A CN 102731352 A CN102731352 A CN 102731352A
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- QRVYABWJVXXOTN-UHFFFAOYSA-N CSc1ccc(C=O)cc1 Chemical compound CSc1ccc(C=O)cc1 QRVYABWJVXXOTN-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N O=Cc(cc1)ccc1Cl Chemical compound O=Cc(cc1)ccc1Cl AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
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
The present invention relates to a kind of compound method of organic cpds, particularly the compound method of 4-methylthio phenyl formaldehyde.
Background technology
4-methylthio phenyl formaldehyde, its molecular formula are C
8H
8OS, its structural formula are shown in S-1, and its pure article are light yellow crystal; Fusing point is 267 ℃; It is a kind of important synthetic dyestuff that can be used for, and the organic intermediate of medicine can be used as cox 2 inhibitor rofecoxib and verivate thereof like it; The raw material of the midbody of NSAIDs Luo Feikao former times etc., of many uses.
The synthetic 4-methylthio group method of benzaldehyde of reporting on the document at present mainly contains following several kinds:
1), be raw material with 4-methylthio phenyl methyl alcohol, make 4-methylthio phenyl formaldehyde through peroxo-, yield reach as high as 100% (Chemistry-A European Journal, 2011,17 (22), p.6056-6060).Reaction formula is following:
2), be raw material with 4-methylsulfinyl phenyl aldehyde, making 4-methylthio phenyl formaldehyde through reduction, yield reach as high as 92% (Tetrahedron Letters, 2009, vol.50 (49), p.6872-6876).Reaction formula is following:
3), with p-bromobenzaldehyde, zinc fluoride is a raw material, DMSO is a solvent; React 36h down at 150 ℃, yield reaches as high as 85% (Chemical Communications (Cambridge, United Kingdom); 2011, vol.47 (18), p.5304-5306).Reaction formula is following:
4), with 4-chloro-benzaldehyde, thiomethyl alcohol, sodium hydroxide are raw material, toluene and water or directly use water as solvent, yield at 80 ~ 100 ℃ of following reaction 3h reach as high as 94% (Huaxue Shijie, 2010, vol.51 (10), p.626-628).Reaction formula is following:
5), with 4-chloro-benzaldehyde, methyl-sulphoxide, Potassium monofluoride are raw material, tetramethylene sulfone is a solvent, 180 ℃ down reaction making 4-methylthio phenyl formaldehyde, yield only be 30% (Chinese Chemical Letters, 2003, vol.14 (3), p.235-238).Reaction formula is following:
6), be raw material with thioanisole etc., DMF is a solvent, at POCl
3Do under the condition of catalyzer, make 4-methylthio phenyl formaldehyde under the normal pressure, yield be merely 14% (Australian Journal of Chemistry, 1979, vol.32 (7), p.1601-12).
More than in the several method of report, first and second kind method is raw materials used to be not easy to obtain, and cost is too high, is not suitable for industrial production; The third method has adopted more expensive p-bromobenzaldehyde, and bromine gets in the waste water as leavings group, and the Atom economy of reaction is bad, and reaction yield is also lower, and temperature of reaction is also higher, and energy consumption is big, is not suitable for suitability for industrialized production; Though the 4th kind of method raw material is simple, in reaction process, can produce great amount of wastewater, unfavorable to environment, the expense of wastewater treatment simultaneously increases, and further causes production cost to increase; The 5th kind and the 6th kind of method yield are too low, are inappropriate for industrial production.
Summary of the invention
The technical problem that the present invention will solve provides the 4-methylthio group method of benzaldehyde that a kind of raw materials cost is low, pollution is little, yield is high.
In order to solve the problems of the technologies described above, the present invention provides a kind of preparation method of 4-methylthio phenyl formaldehyde, may further comprise the steps:
1), preparation SZTA catalyzer:
1., TiCl
4And ZrOCl
28H
2O mixes, and gets mixed solution; ZrOCl
28H
2Zr atom and TiCl among the O
4In the ratio of atomicity of Ti atom be 50 ~ 5:1; That is, nZr:nTi=50 ~ 5:1 (is preferably 40 ~ 10:1);
2., in mixed solution, to drip concentration be the ammoniacal liquor of 0.9 ~ 1.1mol/L, is 9 ~ 10 until pH value, precipitating can appear in the reaction system of gained; Said sedimentary reaction system ageing 22 ~ 26 h under room temperature that contain; Filter, the ageing postprecipitation of gained is carried out repetitive scrubbing, in washings, do not contain Cl
-Till;
3., with step 2. the washing postprecipitation of gained grind to form the powder of particle diameter in 100 ~ 120 ℃ of drying 8 ~ 9 h after being cooled to room temperature less than 0.150mm;
4., with step 3. the powder of gained put into ammonium metavanadate solution dipping 3 ~ 10h that concentration is 0.009 ~ 0.011mol/L, the oven dry back is in 600 ~ 700 ℃ of roasting 2.5 ~ 3.5 h;
5., step gains are 4. put into (the NH that concentration is 0.08 ~ 0.12mol/L
4)
2SO
4Flood 4 ~ 6h in the solution; The oven dry back gets solid acid SO in 450 ~ 550 ℃ of roasting 2.5 ~ 3.5 h
4 2-/ ZrO
2-TiO
2-V
20
5Catalyzer is called for short the SZTA catalyzer;
2), according to the amount ratio of 0.3 ~ 2g SZTA catalyzer/0.1mol thioanisole, in autoclave, add SZTA catalyzer and thioanisole, mixture;
It is 0.5 ~ 5MPa that mixture heating up to 70 ~ 90 ℃ (being preferably 80 ℃) back feeding CO is made the pressure in the autoclave; Insulation reaction 3 ~ 8h; After reaction finishes, reaction product is filtered, the filtrating of gained is hydrolyzed after being cooled to room temperature, gets 4-methylthio phenyl formaldehyde.
Improvement as the preparation method of 4-methylthio phenyl formaldehyde of the present invention: being hydrolyzed to step 2): in the filtrating that the 0.1mol thioanisole is produced, import the water of 40 ~ 60ml, stir 25 ~ 35min under the room temperature, the solid of gained is a 4-methylthio phenyl formaldehyde.
Improvement as the preparation method of 4-methylthio phenyl formaldehyde of the present invention:
Step 1) 4. in oven dry be: in 70 ~ 90 ℃ the oven dry 2.5 ~ 3.5 hours;
Step 1) 5. in oven dry be: in 70 ~ 90 ℃ the oven dry 2.5 ~ 3.5 hours.
Remarks explanations: step 1) 4. in dipping and step 1) 5. in dipping all need guarantee: quilt is soaked the complete submergence of the impregnated liquid of thing and is got final product.
Among the preparation method of 4-methylthio phenyl formaldehyde of the present invention, step 2) reaction can be carried out in the teflon-lined stainless steel autoclave is arranged.Step 2) reaction equation is following:
SZTA catalyzer after the present invention uses is through washing, and alcohol is washed and handled the recyclable utilization in back.Specific as follows:
1. the SZTA catalyzer 0.3g after will using places the beaker of 100ml, adds about 50ml water, after stirring 5min under 100 rev/mins the rotating speed, filters.
2. will place the beaker of 100ml through the SZTA catalyzer after the above-mentioned washing, and add about 50ml ethanol, and after stirring 5min under 100 rev/mins the rotating speed, filter, 80 ℃ of baking 3h get reusable SZTA catalyzer.
Preparing method of the present invention has following advantage:
(1), this method utilizes thioanisole and CO to be raw material, generates 4-methylthio phenyl formaldehyde, the reaction of atomic economy is high, and three-waste free discharge almost, is a kind of eco-friendly method.
(2), this method is utilized solid super-strong acid SO
4 2-/ ZrO
2-TiO
2-V
20
5Make catalyzer, one step of reaction accomplishes, and yield is higher.
(3), used Preparation of Catalyst in this method, reclaim all simplyr, further reduced production cost.
Embodiment
The preparation method of embodiment 1, a kind of 4-methylthio phenyl formaldehyde is a raw material with the thioanisole, carries out following steps successively:
1), SZTA Preparation of catalysts:
1., TiCl
4And ZrOCl
28H
2O mixes, and gets mixed solution; ZrOCl
28H
2Zr atom and TiCl among the O
4In the ratio of atomicity of Ti atom be 10:1; That is nZr:nTi=10:1;
2., stirring fast under (100 rev/mins), be that the ammoniacal liquor of 1mol/L is added dropwise to step 1. in the mixed solution of gained with concentration, be 9 until pH value, precipitating can appear in the reaction system of gained, contains sedimentary reaction system ageing 24 h under room temperature; Filter, the ageing postprecipitation of gained is carried out repetitive scrubbing, in washings, do not contain Cl
-Till;
3., with step 2. the washing postprecipitation of gained grind to form the powder of particle diameter in 110 ℃ of drying 8 h after being cooled to room temperature less than 0.150mm;
4., with step 3. the powder of gained to put into concentration be that the ammonium metavanadate solution of 0.01mol/L floods 5h, oven dry (that is, in 80 ℃ of oven dry 3 hours) back is in 650 ℃ of roasting 3h;
5., step gains are 4. put into (the NH that concentration is 0.1mol/L
4)
2SO
4Dipping 5 h in the solution; Oven dry (that is, in 80 ℃ of oven dry 3 hours) back is in 500 ℃ of roasting 3h; Get solid acid SO
4 2-/ ZrO
2-TiO
2-V
20
5Catalyzer is called for short the SZTA catalyzer.
2), the SZTA catalyzer that takes by weighing 0.3g step 1) gained place 50ml the teflon-lined stainless steel autoclave arranged, add 12ml (0.1mol) thioanisole; Feeding CO after the mixture heating up to 80 that will be made up of SZTA catalyzer and thioanisole ℃, to make the pressure in the autoclave be 0.5MPa, and insulation (80 ℃) reaction 3h is after reaction finishes; Reaction product is filtered; The filtrating of gained is hydrolyzed after being cooled to room temperature,, in the filtrating of gained, imports the water of 50ml that is; Stir 30min down at 100 rev/mins, the solid of gained is a 4-methylthio phenyl formaldehyde.The final 4-methylthio phenyl formaldehyde that gets 11.6g, yield is 76%.
The preparation method of embodiment 2, a kind of 4-methylthio phenyl formaldehyde is a raw material with the thioanisole, carries out following steps successively:
1), SZTA Preparation of catalysts:
1., TiCl
4And ZrOCl
28H
2O mixes, and gets mixed solution; ZrOCl
28H
2Zr atom and TiCl among the O
4In the ratio of atomicity of Ti atom be 20:1; That is nZr:nTi=20:1;
2., stirring fast under (100 rev/mins), be that the ammoniacal liquor of 1mol/L is added dropwise to the 1. mixed solution of gained of step with concentration, be 9 until pH value, precipitating can appear in the reaction system of gained, contains sedimentary reaction system ageing 24 h under room temperature; Filter, the ageing postprecipitation of gained is carried out repetitive scrubbing, in washings, do not contain Cl
-Till;
3., with step 2. the washing postprecipitation of gained grind to form the powder of particle diameter in 110 ℃ of drying 8 h after being cooled to room temperature less than 0.150mm;
4., with step 3. the powder of gained to put into concentration be that the ammonium metavanadate solution of 0.01mol/L floods 6h, oven dry (that is, in 80 ℃ of oven dry 3 hours) back is in 650 ℃ of roasting 3h;
5., step gains are 4. put into (the NH that concentration is 0.1mol/L
4)
2SO
4Dipping 5 h in the solution; Oven dry (that is, in 80 ℃ of oven dry 3 hours) back is in 500 ℃ of roasting 3 h; Get solid acid SO
4 2-/ ZrO
2-TiO
2-V
20
5Catalyzer is called for short the SZTA catalyzer.
2), the SZTA catalyzer that takes by weighing 1g step 1) gained place 50ml the teflon-lined stainless steel autoclave arranged, add 12ml (0.1mol) thioanisole; Feeding CO after the mixture heating up to 80 that will be made up of SZTA catalyzer and thioanisole ℃, to make the pressure in the autoclave be 3MPa, and insulation (80 ℃) reaction 5h is after reaction finishes; Reaction product is filtered; The filtrating of gained is hydrolyzed after being cooled to room temperature,, in the filtrating of gained, imports the water of 50ml that is; Stir 30min down at 100 rev/mins, the solid of gained is a 4-methylthio phenyl formaldehyde.The final 4-methylthio phenyl formaldehyde that gets 14.6g, yield is 96%.
The preparation method of embodiment 3, a kind of 4-methylthio phenyl formaldehyde is a raw material with the thioanisole, carries out following steps successively:
1), SZTA Preparation of catalysts:
With embodiment 1.
2), the SZTA catalyzer that takes by weighing 2g step 1) gained place 50ml the teflon-lined stainless steel autoclave arranged, add 12ml (0.1mol) thioanisole; Feeding CO after the mixture heating up to 80 that will be made up of SZTA catalyzer and thioanisole ℃, to make the pressure in the autoclave be 0.5MPa, and insulation (80 ℃) reaction 3h is after reaction finishes; Reaction product is filtered; The filtrating of gained is hydrolyzed after being cooled to room temperature,, in the filtrating of gained, imports the water of 50ml that is; Stir 30min down at 100 rev/mins, the solid of gained is a 4-methylthio phenyl formaldehyde.The final 4-methylthio phenyl formaldehyde that gets 12.2g, yield is 80.2%.
The preparation method of embodiment 4, a kind of 4-methylthio phenyl formaldehyde is a raw material with the thioanisole, carries out following steps successively:
1), SZTA Preparation of catalysts:
With embodiment 1.
2), the SZTA catalyzer that takes by weighing 0.3g step 1) gained place 50ml the teflon-lined stainless steel autoclave arranged, add 12ml (0.1mol) thioanisole; Feeding CO after the mixture heating up to 80 that will be made up of SZTA catalyzer and thioanisole ℃, to make the pressure in the autoclave be 3MPa, and insulation (80 ℃) reaction 8h is after reaction finishes; Reaction product is filtered; The filtrating of gained is hydrolyzed after being cooled to room temperature,, in the filtrating of gained, imports the water of 50ml that is; Stir 30min down at 100 rev/mins, the solid of gained is a 4-methylthio phenyl formaldehyde.The final 13.0g 4-methylthio phenyl formaldehyde that gets, yield is 85.6%.
The preparation method of embodiment 5, a kind of 4-methylthio phenyl formaldehyde is a raw material with the thioanisole, carries out following steps successively:
1), SZTA Preparation of catalysts:
With embodiment 1.
2), the SZTA catalyzer that takes by weighing 1g step 1) gained place 50ml the teflon-lined stainless steel autoclave arranged, add 12ml (0.1mol) thioanisole; Feeding CO after the mixture heating up to 80 that will be made up of SZTA catalyzer and thioanisole ℃, to make the pressure in the autoclave be 0.5MPa, and insulation (80 ℃) reaction 3h is after reaction finishes; Reaction product is filtered; The filtrating of gained is hydrolyzed after being cooled to room temperature,, in the filtrating of gained, imports the water of 50ml that is; Stir 30min down at 100 rev/mins, the solid of gained is a 4-methylthio phenyl formaldehyde.The final 4-methylthio phenyl formaldehyde that gets 12.0g, yield is 79.0%.
The preparation method of embodiment 6, a kind of 4-methylthio phenyl formaldehyde is a raw material with the thioanisole, carries out following steps successively:
1), SZTA Preparation of catalysts:
With embodiment 2.
2), the SZTA catalyzer that takes by weighing 2g step 1) gained place 50ml the teflon-lined stainless steel autoclave arranged, add 12ml (0.1mol) thioanisole; Feeding CO after the mixture heating up to 80 that will be made up of SZTA catalyzer and thioanisole ℃, to make the pressure in the autoclave be 3MPa, and insulation (80 ℃) reaction 5h is after reaction finishes; Reaction product is filtered; The filtrating of gained is hydrolyzed after being cooled to room temperature,, in the filtrating of gained, imports the water of 50ml that is; Stir 30min down at 100 rev/mins, the solid of gained is a 4-methylthio phenyl formaldehyde.The final 4-methylthio phenyl formaldehyde that gets 13.3g, yield is 87.3%.
The preparation method of embodiment 7, a kind of 4-methylthio phenyl formaldehyde is a raw material with the thioanisole, carries out following steps successively:
1), SZTA Preparation of catalysts:
With embodiment 2.
2), the SZTA catalyzer that takes by weighing 0.3g step 1) gained place 50ml the teflon-lined stainless steel autoclave arranged, add 12ml (0.1mol) thioanisole; Feeding CO after the mixture heating up to 80 that will be made up of SZTA catalyzer and thioanisole ℃, to make the pressure in the autoclave be 5MPa, and insulation (80 ℃) reaction 5h is after reaction finishes; Reaction product is filtered; The filtrating of gained is hydrolyzed after being cooled to room temperature,, in the filtrating of gained, imports the water of 50ml that is; Stir 30min down at 100 rev/mins, the solid of gained is a 4-methylthio phenyl formaldehyde.The final 4-methylthio phenyl formaldehyde that gets 13.7g, yield is 90.2%.
The preparation method of embodiment 8, a kind of 4-methylthio phenyl formaldehyde is a raw material with the thioanisole, carries out following steps successively:
1), SZTA Preparation of catalysts:
With embodiment 2.
2), the SZTA catalyzer that takes by weighing 2g step 1) gained place 50ml the teflon-lined stainless steel autoclave arranged, add 12ml (0.1mol) thioanisole; Feeding CO after the mixture heating up to 80 that will be made up of SZTA catalyzer and thioanisole ℃, to make the pressure in the autoclave be 5MPa, and insulation (80 ℃) reaction 8h is after reaction finishes; Reaction product is filtered; The filtrating of gained is hydrolyzed after being cooled to room temperature,, in the filtrating of gained, imports the water of 50ml that is; Stir 30min down at 100 rev/mins, the solid of gained is a 4-methylthio phenyl formaldehyde.The final 4-methylthio phenyl formaldehyde that gets 14.7g, yield is 96.6%.
The preparation method of embodiment 9, a kind of 4-methylthio phenyl formaldehyde is a raw material with the thioanisole, carries out following steps successively:
1), SZTA Preparation of catalysts:
With embodiment 1.
2), the SZTA catalyzer that takes by weighing 2g step 1) gained place 50ml the teflon-lined stainless steel autoclave arranged, add 12ml (0.1mol) thioanisole; Feeding CO after the mixture heating up to 80 that will be made up of SZTA catalyzer and thioanisole ℃, to make the pressure in the autoclave be 5MPa, and insulation (80 ℃) reaction 8h is after reaction finishes; Reaction product is filtered; The filtrating of gained is hydrolyzed after being cooled to room temperature,, in the filtrating of gained, imports the water of 50ml that is; Stir 30min down at 100 rev/mins, the solid of gained is a 4-methylthio phenyl formaldehyde.The final 4-methylthio phenyl formaldehyde that gets 14.2g, yield is 93.5%.
The preparation method of Comparative Examples 1, a kind of 4-methylthio phenyl formaldehyde, the cancellation embodiment 2 step 1), with step 2) in 1g SZTA catalyzer make 1g POCl into
3, all the other are fully with embodiment 2.The final 4-methylthio phenyl formaldehyde that gets 8.36g, yield is 55%.
The preparation method of Comparative Examples 2, a kind of 4-methylthio phenyl formaldehyde, the cancellation embodiment 2 step 1), with step 2) in 1g SZTA catalyzer make 2g POCl into
3, all the other are fully with embodiment 2.The final 4-methylthio phenyl formaldehyde that gets 8.82g, yield is 58%.
The preparation method of Comparative Examples 3, a kind of 4-methylthio phenyl formaldehyde, the cancellation embodiment 2 step 1), with step 2) in 1g SZTA catalyzer make 1g POCl into
3, reaction pressure changes 5MPa into, and the reaction times is 8h, and all the other are fully with embodiment 2.The final 4-methylthio phenyl formaldehyde that gets 9.58g, yield is 58%.
The preparation method of Comparative Examples 4, a kind of 4-methylthio phenyl formaldehyde changes the step of embodiment 2 Zr and the atomicity ratio of Ti in 1. into nZr:nTi=50:1, and all the other are fully with embodiment 2.The final 4-methylthio phenyl formaldehyde that gets 10.4g, yield is 68.4%.
The preparation method of Comparative Examples 5, a kind of 4-methylthio phenyl formaldehyde changes the step of embodiment 2 Zr and the atomicity ratio of Ti in 1. into nZr:nTi=40:1, and all the other are fully with embodiment 2.The final 4-methylthio phenyl formaldehyde that gets 11.34g, yield is 74.6%.
The preparation method of Comparative Examples 6, a kind of 4-methylthio phenyl formaldehyde changes the step of embodiment 2 Zr and the atomicity ratio of Ti in 1. into nZr:nTi=30:1, and all the other are fully with embodiment 2.The final 4-methylthio phenyl formaldehyde that gets 12.51g, yield is 82.3%.
The preparation method of Comparative Examples 7, a kind of 4-methylthio phenyl formaldehyde changes the step of embodiment 2 Zr and the atomicity ratio of Ti in 1. into nZr:nTi=5:1, and all the other are fully with embodiment 2.The final 4-methylthio phenyl formaldehyde that gets 9.13g, yield is 60.1%.
At last, it is also to be noted that what more than enumerate only is several specific embodiments of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be arranged.All distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention all should be thought protection scope of the present invention.
Claims (3)
1.4-the preparation method of methylthio phenyl formaldehyde is characterized in that may further comprise the steps:
1), preparation SZTA catalyzer:
1., TiCl
4And ZrOCl
28H
2O mixes, and gets mixed solution; Said ZrOCl
28H
2Zr atom and TiCl among the O
4In the ratio of atomicity of Ti atom be 50 ~ 5:1;
2., in said mixed solution, to drip concentration be the ammoniacal liquor of 0.9 ~ 1.1mol/L, is 9 ~ 10 until pH value, precipitating can appear in the reaction system of gained; Said sedimentary reaction system ageing 22 ~ 26 h under room temperature that contain; Filter, the ageing postprecipitation of gained is carried out repetitive scrubbing, in washings, do not contain Cl
-Till;
3., with step 2. the washing postprecipitation of gained grind to form the powder of particle diameter in 100 ~ 120 ℃ of drying 8 ~ 9 h after being cooled to room temperature less than 0.150mm;
4., with step 3. the powder of gained put into ammonium metavanadate solution dipping 3 ~ 10h that concentration is 0.009 ~ 0.011mol/L, the oven dry back is in 600 ~ 700 ℃ of roasting 2.5 ~ 3.5 h;
5., step gains are 4. put into (the NH that concentration is 0.08 ~ 0.12mol/L
4)
2SO
4Flood 4 ~ 6h in the solution; The oven dry back gets solid acid SO in 450 ~ 550 ℃ of roasting 2.5 ~ 3.5 h
4 2-/ ZrO
2-TiO
2-V
20
5Catalyzer is called for short the SZTA catalyzer;
2), according to the amount ratio of 0.3 ~ 2g SZTA catalyzer/0.1mol thioanisole, in autoclave, add SZTA catalyzer and thioanisole, mixture;
To make the pressure in the autoclave be 0.5 ~ 5MPa with feeding CO behind said mixture heating up to 70 ~ 90 ℃; Insulation reaction 3 ~ 8h; After reaction finishes, reaction product is filtered, the filtrating of gained is hydrolyzed after being cooled to room temperature, gets 4-methylthio phenyl formaldehyde.
2. the preparation method of 4-methylthio phenyl formaldehyde according to claim 1; It is characterized in that: being hydrolyzed to said step 2): the water that in the filtrating that the 0.1mol thioanisole is produced, imports 40 ~ 60ml; Stir 25 ~ 35min under the room temperature, the solid of gained is a 4-methylthio phenyl formaldehyde.
3. the preparation method of 4-methylthio phenyl formaldehyde according to claim 1 and 2 is characterized in that:
Said step 1) 4. in oven dry be: in 70 ~ 90 ℃ the oven dry 2.5 ~ 3.5 hours;
Said step 1) 5. in oven dry be: in 70 ~ 90 ℃ the oven dry 2.5 ~ 3.5 hours.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115772105A (en) * | 2022-11-08 | 2023-03-10 | 厦门大学 | Synthesis method of 4-nitroanisole |
| CN117486768A (en) * | 2023-12-29 | 2024-02-02 | 山东国邦药业有限公司 | Preparation method of p-methylthiobenzaldehyde |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115772105A (en) * | 2022-11-08 | 2023-03-10 | 厦门大学 | Synthesis method of 4-nitroanisole |
| CN117486768A (en) * | 2023-12-29 | 2024-02-02 | 山东国邦药业有限公司 | Preparation method of p-methylthiobenzaldehyde |
| CN117486768B (en) * | 2023-12-29 | 2024-04-12 | 山东国邦药业有限公司 | Preparation method of p-methylthiobenzaldehyde |
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