CN102992982A - Synthesis method of p-hydroxybenzaldehyde - Google Patents
Synthesis method of p-hydroxybenzaldehyde Download PDFInfo
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- CN102992982A CN102992982A CN2012105343723A CN201210534372A CN102992982A CN 102992982 A CN102992982 A CN 102992982A CN 2012105343723 A CN2012105343723 A CN 2012105343723A CN 201210534372 A CN201210534372 A CN 201210534372A CN 102992982 A CN102992982 A CN 102992982A
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- hydroxybenzaldehyde
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- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 title claims abstract description 103
- 238000001308 synthesis method Methods 0.000 title abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000002994 raw material Substances 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 17
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 claims abstract description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 96
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 238000010189 synthetic method Methods 0.000 claims description 19
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 7
- 238000009413 insulation Methods 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 8
- 238000000746 purification Methods 0.000 abstract description 6
- 239000006227 byproduct Substances 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 description 17
- 238000005303 weighing Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 2
- 229960003022 amoxicillin Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
- 238000004080 punching Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 2
- DYHOLQACRGJEHX-CYBMUJFWSA-N (-)-Farrerol Natural products C1([C@@H]2OC3=C(C)C(O)=C(C(=C3C(=O)C2)O)C)=CC=C(O)C=C1 DYHOLQACRGJEHX-CYBMUJFWSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- YRSSHOVRSMQULE-UHFFFAOYSA-N 3,5-dichloro-4-hydroxybenzonitrile Chemical compound OC1=C(Cl)C=C(C#N)C=C1Cl YRSSHOVRSMQULE-UHFFFAOYSA-N 0.000 description 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
- 239000005489 Bromoxynil Substances 0.000 description 1
- 235000014493 Crataegus Nutrition 0.000 description 1
- 241001092040 Crataegus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DZTRDRPCROOSOG-UHFFFAOYSA-N Matteucinol Natural products C1=CC(OC)=CC=C1C1OC2=C(C)C(O)=C(C)C(O)=C2C(=O)C1 DZTRDRPCROOSOG-UHFFFAOYSA-N 0.000 description 1
- NPWGWQRXHVJJRD-UHFFFAOYSA-N N-hydroxyglycine Chemical compound ONCC(O)=O NPWGWQRXHVJJRD-UHFFFAOYSA-N 0.000 description 1
- 240000007651 Rubus glaucus Species 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- UCKZMPLVLCKKMO-LHLIQPBNSA-N cephamycin Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](C)[C@]21OC UCKZMPLVLCKKMO-LHLIQPBNSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- DYHOLQACRGJEHX-ZDUSSCGKSA-N farrerol Chemical compound C1([C@H]2OC3=C(C)C(O)=C(C(=C3C(=O)C2)O)C)=CC=C(O)C=C1 DYHOLQACRGJEHX-ZDUSSCGKSA-N 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229940081310 piperonal Drugs 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 1
- YIBXWXOYFGZLRU-UHFFFAOYSA-N syringic aldehyde Natural products CC12CCC(C3(CCC(=O)C(C)(C)C3CC=3)C)C=3C1(C)CCC2C1COC(C)(C)C(O)C(O)C1 YIBXWXOYFGZLRU-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a synthesis method of p-hydroxybenzaldehyde. Phenol used as a raw material reacts with a Vilsmeier reagent to synthesize p-hydroxybenzaldehyde. The invention has advantages of easily available raw materials, short reaction period, simple operation, mild reaction conditions, safe reaction process and low requirement on equipment, and is more suitable for industrial production of p-hydroxybenzaldehyde compared to other synthesis method of p-hydroxybenzaldehyde; no by-product is generated in the synthesis process, and separation and purification in a post treatment process is simple, so as to lower the cost of post treatment, and enhance yield and purity of the target product p-hydroxybenzaldehyde, wherein the yield is higher than 90%, and the purity is above 98%; and the synthesis method resolves problems in existing phenol method for p-hydroxybenzaldehyde synthesis, such as difficulties in separation and purification in post treatment, low yield of p-hydroxybenzaldehyde and high cost.
Description
Technical field
The invention belongs to the fine chemical technology field, relate to the chemical synthetic method, be specifically related to the synthetic method of p-Hydroxybenzaldehyde.
Background technology
P-Hydroxybenzaldehyde is the important intermediate of medicine industry and perfume industry, in medicine industry, can be used for synthetic amoxycillin (amoxycilline Trihydrate bp), Trimethoprim Trimethyl phosphate (TMP), 3,4,5-TMB, to hydroxyglycine, amoxycillin cephamycin, artificial rhizoma Gastrodiae, farrerol, Ai Siluo etc.; In perfume industry for the synthesis of spices such as vanillin food grade,1000.000000ine mesh, vanirone, piperonal, syringic aldehyde, aubepine and raspberry ketones.Also be used for abroad the synthetic of pesticide herbicide bromoxynil and chloroxynil, and produce sterilant, photograph emulsifying agent, nickel plating gloss-imparting agent, liquid crystal etc.
Present industrial production p-Hydroxybenzaldehyde is the operational path take phenol, p-cresol, para-nitrotoluene etc. as raw material mainly.Existing phynol method raw material is easy to get, and manufacturing process is simpler, but the separation in later stage and purification ratio are difficult, cause the yield of p-Hydroxybenzaldehyde on the low side, and cost is higher.
Summary of the invention
The object of the present invention is to provide a kind of take phenol as raw material, by the synthetic p-Hydroxybenzaldehyde of simple technique, this synthetic method feed stock conversion is high, product yield is high, it is a kind of brand-new method for preparing p-Hydroxybenzaldehyde take phenol as raw material, namely adopt Vilsmeier reagent and phenol reactant to prepare p-Hydroxybenzaldehyde, having solved in the synthetic p-Hydroxybenzaldehyde technique of existing phynol method exists the later stage to separate and purification difficult, cause the yield of p-Hydroxybenzaldehyde on the low side, the problem that cost is higher.
The invention provides a kind of synthetic method of p-Hydroxybenzaldehyde, take phenol as raw material, adopt Vilsmeier reagent and phenol reactant to prepare p-Hydroxybenzaldehyde, reaction equation is as follows:
Concrete steps comprise:
(1) take toluene as solvent, adding DMF and reagent I is 10～30 ℃ of lower reactions in temperature, gets Vilsmeier reagent;
(2) phenol is slowly added in the Vilsmeier reagent that generates in the step (1) and carry out insulation reaction, be cooled to 25 ℃-50 ℃, add again the water stirring reaction;
(3) add water washing, separatory, desolventizing, drying after reaction is finished, get faint yellow solid, be target product.
The composition principle of described p-Hydroxybenzaldehyde is:
The synthetic method of the p-Hydroxybenzaldehyde that the present invention relates to is a kind of brand-new method for preparing p-Hydroxybenzaldehyde take phenol as raw material, namely adopts Vilsmeier reagent and phenol reactant to prepare p-Hydroxybenzaldehyde.From thermodynamics, Vilsmeier reagent and phenol reactant generate the contraposition product p-Hydroxybenzaldehyde of phenol at first, and at this moment aldehyde radical occupies the contraposition position of phenyl ring, and the aldehyde radical in the contraposition produces so do not have other by products so that the phenyl ring passivation.
Reagent I is POCl in the described step (1)
3Or SOCl
2Or PCl
5Or PCl
3A kind of.
The volumetric usage of the middle toluene of described step (1) is 3～10 times of DMF.
Phenol: DMF in described step (1) and the step (2): the mol ratio of reagent I is 1:1～1.2:1～1.3, and the very few reaction of raw material is incomplete, and excessive cost increases, and by product is increased.
Order of addition(of ingredients) in the described step (1) is to add reagent I in the toluene to drip DMF again, or reagent I is added drop-wise in the mixed solution of toluene and DMF.This is because the reaction in the step (1) is strong exothermal reaction, can only be that a kind of raw material is added drop-wise in the another kind of raw material, is conducive to like this temperature of reaction of the hierarchy of control.
The temperature of reaction of system is 10～30 ℃ in the described step (1).Because the reaction of system is more violent in the step (1), heat release is many, and wayward reaction during excess Temperature can make temperature moment rising that the punching material occurs, so temperature is controlled in this scope.
The adding method of phenol is adding phenol solid in the described step (2), or adds the toluene solution of phenol.
Temperature of reaction in the described step (2) is 60～110 ℃, is preferably 110 ℃.When temperature was lower than 60 ℃, the meeting augmenting response time, energy consumption increased; Because the boiling point of toluene is 110 ℃, selection toluene is solvent, and when carrying out back flow reaction, best temperature of reaction is 110 ℃.
Reaction times in the described step (2) is 30min～180min, and this is the Best Times scope of reaction, and the time is too short, causes reaction not exclusively, and product yield is excessively low, and cost increases; Overlong time can increase energy consumption, and corresponding cost also can increase.
The temperature of the water that adds in the described step (2) is 0-83 ℃, finds through the long-term a large amount of test of contriver, when the temperature of the water that adds during greater than 83 ℃, bumping even punching material phenomenon can occur.
Washing temperature is 40～80 ℃ in the described step (3), crosses when low when washing temperature, and the product in the toluene can be separated out, and when washing temperature is too high, reaches the azeotropic point of toluene and water, and is dangerous.General washing two to three times because product is dissolved in the toluene, is got the upper toluene phase, desolvation toluene under negative pressure, and recovery toluene is also applied mechanically, and gets at last faint yellow solid, and detecting the gained faint yellow solid by liquid matter and nucleus magnetic hydrogen spectrum is p-Hydroxybenzaldehyde.Separation and purification operations in the post-processed process are simple, and the solvent toluene after the recovery can be applied mechanically, and have reduced the cost of post-processed, thereby have reduced production cost.
The present invention is as raw material take phenol, prepare p-Hydroxybenzaldehyde with Vilsmeier reagent, raw material is easy to get, reaction time is short, operation steps is simple, and reaction conditions is gentle, reaction process safety, low for equipment requirements, the method for other p-Hydroxybenzaldehydes more is applicable to industrial production p-Hydroxybenzaldehyde relatively; In building-up process, there is not by product to produce, separating-purifying is simple in the post-processed process, reduced the cost of post-processed, yield and the purity of target product p-Hydroxybenzaldehyde have been improved, yield is more than 90%, and purity is more than 98%, solved in the synthetic p-Hydroxybenzaldehyde method of existing phynol method to exist the later stage to separate and purification difficult, cause the yield of p-Hydroxybenzaldehyde on the low side, the problem that cost is higher.
Embodiment
Below in conjunction with specific embodiment invention is described further, but not as to the restriction of summary of the invention, all based on purification principle of the present invention technology all belong to integral part of the present invention.
Embodiment one
The synthetic method of p-Hydroxybenzaldehyde, take phenol as raw material, concrete steps comprise:
(1) in the four-hole boiling flask of drying, adds 300mL toluene, then add 100mL DMF, measure 93.79mL SOCl
2In constant pressure funnel, in four-hole boiling flask, drip SOCl
2, temperature of reaction is 30 ℃, stirs 30min, gets Vilsmeier reagent;
(2) taking by weighing 121.68g phenol and add in the four-hole boiling flask, is 60 ℃ of lower insulation reaction 80min in temperature, cools to 50 ℃ again, and the adding volume is that 250mL, temperature are 83 ℃ water stirring 100min;
(3) solution in step (2) four-hole boiling flask is moved in the separating funnel leave standstill, cut lower floor's water, the water that adds volume and be 300mL, temperature and be 80 ℃ is washed; Then cut lower floor's water, get toluene and remove toluene under negative pressure, drying gets faint yellow solid, namely obtains p-Hydroxybenzaldehyde 143.85g, purity 98.9%, yield 91.1%.
Embodiment two
The synthetic method of p-Hydroxybenzaldehyde, take phenol as raw material, concrete steps comprise:
(1) in the four-hole boiling flask of drying, adds 100mL toluene, then add 12.05mL POCL
3, measure 10mL DMF in constant pressure funnel, in four-hole boiling flask, drip DMF, temperature of reaction is 10 ℃, stirs 45min, gets Vilsmeier reagent;
(2) taking by weighing 10.15g phenol and add in the four-hole boiling flask, is 110 ℃ of lower insulation reaction 30min in temperature, cools to 25 ℃ again, and the adding volume is that 200mL, temperature are 0 ℃ water stirring 100min;
(3) solution in step (2) four-hole boiling flask is moved in the separating funnel leave standstill, cut lower floor's water, the water that adds volume and be 280mL, temperature and be 60 ℃ is washed; Then cut lower floor's water, get toluene and remove toluene under negative pressure, drying gets faint yellow solid, namely obtains p-Hydroxybenzaldehyde 12.21g, purity 98.7%, yield 92.7%.
Embodiment three
The synthetic method of p-Hydroxybenzaldehyde, take phenol as raw material, concrete steps comprise:
(1) in the four-hole boiling flask of drying, adds 200mL toluene, then add 48.61mL PCL
5, measure 50mL DMF in constant pressure funnel, in four-hole boiling flask, drip DMF, temperature of reaction is 20 ℃, stirs 70min, gets Vilsmeier reagent;
(2) taking by weighing 60.84g phenol and be dissolved in the 100mL toluene solution and add in the four-hole boiling flask, is 85 ℃ of lower insulation reaction 180min in temperature, cools to 40 ℃ again, and addings volume is that 150mL, temperature are 40 ℃ water stirring 65min;
(3) solution in step (2) four-hole boiling flask is moved in the separating funnel leave standstill, cut lower floor's water, the water that adds volume and be 180mL, temperature and be 40 ℃ is washed; Then cut lower floor's water, get toluene and remove toluene under negative pressure, drying gets faint yellow solid, namely obtains p-Hydroxybenzaldehyde 73.18g, purity 98.4%, yield 92.7%.
Embodiment four
The synthetic method of p-Hydroxybenzaldehyde, take phenol as raw material, concrete steps comprise:
(1) in the four-hole boiling flask of drying, adds 300mL toluene, then add 60mL DMF, measure 73.33mL PCL
3In constant pressure funnel, in four-hole boiling flask, drip PCL
3, temperature of reaction is 15 ℃, stirs 70min, gets Vilsmeier reagent;
(2) taking by weighing 60.84g phenol and add in the four-hole boiling flask, is 100 ℃ of lower insulation reaction 60min in temperature, cools to 30 ℃ again, and the adding volume is that 150mL, temperature are 60 ℃ water stirring 65min;
(3) solution in step (2) four-hole boiling flask is moved in the separating funnel leave standstill, cut lower floor's water, the water that adds volume and be 200mL, temperature and be 50 ℃ is washed; Then cut lower floor's water, get toluene and remove toluene under negative pressure, drying gets faint yellow solid, namely obtains p-Hydroxybenzaldehyde 72.55g, purity 98.1%, yield 91.9%.
Can find out that from embodiment 1-4 take phenol as raw material, adopt the synthetic p-Hydroxybenzaldehyde of the present invention, the purity of gained p-Hydroxybenzaldehyde is more than 98%, yield is more than 90%.
Claims (9)
1. the synthetic method of a p-Hydroxybenzaldehyde take phenol as raw material, is characterized in that: adopt Vilsmeier reagent and phenol reactant to prepare p-Hydroxybenzaldehyde, reaction equation is as follows:
2. the synthetic method of p-Hydroxybenzaldehyde according to claim 1, it is characterized in that: concrete steps comprise:
(1) take toluene as solvent, adding DMF and reagent I is 10～30 ℃ of lower reactions in temperature, gets Vilsmeier reagent;
(2) phenol is slowly added in the Vilsmeier reagent that generates in the step (1) and carry out insulation reaction, be cooled to 25 ℃-50 ℃, add again the water stirring reaction;
(3) add water washing, separatory, desolventizing, drying after reaction is finished, get faint yellow solid, be target product.
3. the synthetic method of p-Hydroxybenzaldehyde according to claim 2 is characterized in that: reagent I is POCl in the described step (1)
3Or SOCl
2Or PCl
5Or PCl
3A kind of.
4. the synthetic method of p-Hydroxybenzaldehyde according to claim 2 is characterized in that: the volumetric usage of toluene is 3～10 times of DMF in the described step (1).
5. the synthetic method of p-Hydroxybenzaldehyde according to claim 2 is characterized in that: phenol: DMF in described step (1) and the step (2): the mol ratio of reagent I is 1:1～1.2:1～1.3.
6. the synthetic method of p-Hydroxybenzaldehyde according to claim 2 is characterized in that: the order of addition(of ingredients) in the described step (1) is to add reagent I in the toluene to drip DMF again, or reagent I is added drop-wise in the mixed solution of toluene and DMF.
7. the synthetic method of p-Hydroxybenzaldehyde according to claim 2 is characterized in that: the adding method of phenol or adds the toluene solution of phenol for adding the phenol solid in the described step (2).
8. the synthetic method of p-Hydroxybenzaldehyde according to claim 2, it is characterized in that: the temperature of reaction in the described step (2) is 60～110 ℃.
9. the synthetic method of p-Hydroxybenzaldehyde according to claim 2, it is characterized in that: the reaction times in the described step (2) is 30min～180min.
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Cited By (6)
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| CN103787945A (en) * | 2014-01-20 | 2014-05-14 | 天津市敬业精细化工有限公司 | Preparation method of aromatic aldehyde |
| CN104230748A (en) * | 2014-11-04 | 2014-12-24 | 洛阳市三诺化工有限公司 | Synthetic process of copper extraction agent 5-nonyl salicylaldoxime |
| CN104230748B (en) * | 2014-11-04 | 2017-01-04 | 洛阳市三诺化工有限公司 | A kind of synthesis technique of copper extractant 5-nonyl salicyl aldooxime |
| CN106916051A (en) * | 2017-02-21 | 2017-07-04 | 新乡学院 | A kind of preparation method of the hydroxy-benzyl alcohol of 3,5 di-t-butyl 4 |
| CN112205405A (en) * | 2020-11-11 | 2021-01-12 | 浙江新安化工集团股份有限公司 | Weeding composition containing vanillin and glufosinate-ammonium and herbicide |
| CN112616837A (en) * | 2020-10-28 | 2021-04-09 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | Use of o-hydroxy-p-methoxybenzaldehyde derivatives as herbicides |
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