CN109761889A - A kind of synthetic method of 4- pyridinemethanol - Google Patents
A kind of synthetic method of 4- pyridinemethanol Download PDFInfo
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- CN109761889A CN109761889A CN201711095592.XA CN201711095592A CN109761889A CN 109761889 A CN109761889 A CN 109761889A CN 201711095592 A CN201711095592 A CN 201711095592A CN 109761889 A CN109761889 A CN 109761889A
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- acetic acid
- pyridinemethanol
- picolyl
- nitric oxide
- pyridine
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Abstract
The present invention relates to organic chemistry filed, specifically a kind of synthetic method of 4- pyridinemethanol includes the following steps；Using 4- picoline as raw material, in acid condition, 4- pyridine nitric oxide is obtained by oxidation reaction；The 4- pyridine nitric oxide resets synthesis of acetic acid -4- picolyl by the way that aceticanhydride is acylated；Acetic acid -4- the picolyl hydrolyzes to obtain 4- pyridinemethanol.A kind of synthetic method of 4- pyridinemethanol of the invention reduces cost while having the advantages that 1, can obtain preferable hydrolysis rate using the potassium hydroxide solution of mass percent 20%；2, using hydrogen peroxide as oxidant, oxidizing condition is mild, at low cost, fully reacting；3, total recovery of the present invention is high, and production cost is low, is easy to industrial scale production.
Description
Technical field
The present invention relates to organic chemistry filed, specifically a kind of synthetic method of 4- pyridinemethanol.
Background technique
4- pyridinemethanol has wide range of applications as important medicine intermediate and fine chemical material, and market is advanced wide
It is wealthy.In medicine, it can be used to synthesize change-blood as the 4- pyridinemethanol of important medicine intermediate and want Bisacody, and synthesis
The raw material of organophosphorus compounds antidote pralidoxime.Agriculturally, 4- pyridine carboxaldehyde is that synthesis is some acaricidal necessary intermediate
Body；Photosensitive industrial, 4- pyridine carboxaldehyde can be used for synthesizing nitrogen-containing heterocycle class color photographic material.Therefore, develop it is at low cost,
Preparation method that is high-efficient and being suitable for industrial 4- pyridinemethanol is always the direction that scientific research personnel makes great efforts.
Summary of the invention
It is at low cost the technical problem to be solved by the invention is to provide a kind of high income, the mild 4- pyridine of reaction condition
The synthetic method of methanol.
In order to solve the above technical problems, a kind of synthetic method of 4- pyridine carboxaldehyde of the invention includes the following steps；
Using 4- picoline as raw material, in acid condition, 4- pyridine nitric oxide is obtained by oxidation reaction；
The 4- pyridine nitric oxide resets synthesis of acetic acid -4- picolyl by the way that aceticanhydride is acylated；
Acetic acid -4- the picolyl hydrolyzes to obtain 4- pyridinemethanol.
Further, the acetic acid -4- picolyl hydrolyzes under alkaline condition obtains 4- pyridinemethanol.
Further, the 4- picoline is reacted with glacial acetic acid and hydrogen peroxide, and reaction temperature is 70 DEG C, the reaction time
14h, the 4- picoline, glacial acetic acid, hydrogen peroxide molar ratio be 1:3.5:3, obtain 4- pyridine nitric oxide；
The 4- pyridine nitric oxide is reacted with aceticanhydride, and reaction temperature is 85 DEG C, reaction time 6h, the 4- pyridine nitrogen
The molar ratio of oxide and aceticanhydride is 1:2.5, obtains acetic acid -4- picolyl；
Acetic acid -4- the picolyl is reacted with potassium hydroxide solution, reaction time 4h, the acetic acid -2- pyridine first
The molar ratio of ester and potassium hydroxide is 1:1.5, and reaction obtains 4- pyridinemethanol.
Further, the 4- picoline is reacted with glacial acetic acid and hydrogen peroxide, and reaction temperature is 73 DEG C, the reaction time
13h, the 4- picoline, glacial acetic acid, hydrogen peroxide molar ratio be 1:3.5:2.5, obtain 4- pyridine nitric oxide；
The 2- pyridine nitric oxide is reacted with aceticanhydride, and reaction temperature is 93 DEG C, reaction time 5h, the 4- pyridine nitrogen
The molar ratio of oxide and aceticanhydride is 1:3, obtains acetic acid -4- picolyl；
Acetic acid -4- the picolyl is reacted with potassium hydroxide solution, reaction time 4h, the acetic acid -4- pyridine first
The molar ratio of ester and potassium hydroxide is 1:1.7, and reaction obtains 4- pyridinemethanol.
Further, the mass percent of the potassium hydroxide solution is 20%.
A kind of synthetic method of 4- pyridinemethanol of the invention has the advantages that 1, using mass percent 20%
Potassium hydroxide solution reduce cost while can obtain preferable hydrolysis rate；2, using hydrogen peroxide as oxidant, oxidizing condition
Mildly, at low cost, fully reacting；3, total recovery of the present invention is high, and production cost is low, is easy to industrial scale production.
Specific embodiment
Below in conjunction with specific embodiment, the present invention is further illustrated.
The synthetic method of 4- pyridinemethanol of the invention the following steps are included:
(a) using 4- picoline as raw material, in acid condition, 4- pyridine nitric oxide is obtained by oxidation reaction；
(b) the 4- pyridine nitric oxide resets synthesis of acetic acid -4- picolyl by the way that aceticanhydride is acylated；
(c) acetic acid -4- picolyl hydrolyzes to obtain 4- pyridinemethanol.
Preferably, step (c) of the present invention acetic acid -4- picolyl hydrolyzes under alkaline condition obtains 4- pyridinemethanol,
Because acetic acid -4- picolyl hydrolyzed under basic conditions obtains 4- pyridinemethanol and salt, and hydrolyzes to obtain 4- in acid condition
Pyridinemethanol and acid；So the product extraction of acetic acid -4- picolyl under alkaline condition is simpler.
Embodiment one:
(a) the 4- picoline is reacted with glacial acetic acid and hydrogen peroxide, and reaction temperature is 70 DEG C, reaction time 14h, described
4- picoline, glacial acetic acid, hydrogen peroxide molar ratio be 1:3.5:3, obtain 4- pyridine nitric oxide；
(b) the 4- pyridine nitric oxide is reacted with aceticanhydride, and reaction temperature is 85 DEG C, reaction time 6h, the 4- pyrrole
The molar ratio of pyridine nitrogen oxides and aceticanhydride is 1:2.5, obtains acetic acid -4- picolyl；
(c) acetic acid -4- picolyl is reacted with potassium hydroxide solution, reaction time 4h, the acetic acid -2- pyridine
The molar ratio of methyl esters and potassium hydroxide is 1:1.5, and reaction obtains 4- pyridinemethanol.
Reaction equation is as follows:
Embodiment two:
(a) the 4- picoline is reacted with glacial acetic acid and hydrogen peroxide, and reaction temperature is 73 DEG C, reaction time 13h, described
4- picoline, glacial acetic acid, hydrogen peroxide molar ratio be 1:3.5:2.5, obtain 4- pyridine nitric oxide；
(b) the 2- pyridine nitric oxide is reacted with aceticanhydride, and reaction temperature is 93 DEG C, reaction time 5h, the 4- pyrrole
The molar ratio of pyridine nitrogen oxides and aceticanhydride is 1:3, obtains acetic acid -4- picolyl；
(c) acetic acid -4- picolyl is reacted with potassium hydroxide solution, reaction time 4h, the acetic acid -4- pyridine
The molar ratio of methyl esters and potassium hydroxide is 1:1.7, and reaction obtains 4- pyridinemethanol.
Embodiment two is identical as the reaction equation of embodiment one, and difference is the proportion and reaction condition of reactant
Variation.In addition, the optimal mass percent of the potassium hydroxide solution is 20% in embodiment one and embodiment two,
Cost is reduced while preferable hydrolysis rate can be obtained in this way.
It is to be understood that foregoing invention content and specific embodiment are intended to prove technical solution provided by the present invention
Practical application should not be construed as limiting the scope of the present invention.Those skilled in the art are in spirit and principles of the present invention
It is interior, when can various modifications may be made, equivalent replacement or improve.Protection scope of the present invention is subject to the appended claims.
Claims (5)
1. a kind of synthetic method of 4- pyridinemethanol, it is characterised in that: include the following steps；
Using 4- picoline as raw material, in acid condition, 4- pyridine nitric oxide is obtained by oxidation reaction；
The 4- pyridine nitric oxide resets synthesis of acetic acid -4- picolyl by the way that aceticanhydride is acylated；
Acetic acid -4- the picolyl hydrolyzes to obtain 4- pyridinemethanol.
2. a kind of synthetic method of 4- pyridinemethanol described in accordance with the claim 1, it is characterised in that:
Acetic acid -4- the picolyl hydrolyzes under alkaline condition obtains 4- pyridinemethanol.
3. a kind of synthetic method of 4- pyridinemethanol according to claim 2, it is characterised in that:
The 4- picoline is reacted with glacial acetic acid and hydrogen peroxide, and reaction temperature is 70 DEG C, reaction time 14h, the 4- methyl
Pyridine, glacial acetic acid, hydrogen peroxide molar ratio be 1:3.5:3, obtain 4- pyridine nitric oxide；
The 4- pyridine nitric oxide is reacted with aceticanhydride, and reaction temperature is 85 DEG C, reaction time 6h, the 4- N-oxide
The molar ratio of object and aceticanhydride is 1:2.5, obtains acetic acid -3- picolyl；
Acetic acid -4- the picolyl is reacted with potassium hydroxide solution, reaction time 4h, the acetic acid -2- picolyl with
The molar ratio of potassium hydroxide is 1:1.5, and reaction obtains 4- pyridinemethanol.
4. a kind of synthetic method of 4- pyridinemethanol according to claim 2, it is characterised in that:
The 4- picoline is reacted with glacial acetic acid and hydrogen peroxide, and reaction temperature is 73 DEG C, reaction time 13h, the 4- methyl
Pyridine, glacial acetic acid, hydrogen peroxide molar ratio be 1:3.5:2.5, obtain 4- pyridine nitric oxide；
The 4- pyridine nitric oxide is reacted with aceticanhydride, and reaction temperature is 93 DEG C, reaction time 5h, the 4- N-oxide
The molar ratio of object and aceticanhydride is 1:3, obtains acetic acid -4- picolyl；
Acetic acid -4- the picolyl is reacted with potassium hydroxide solution, reaction time 4h, the acetic acid -4- picolyl with
The molar ratio of potassium hydroxide is 1:1.7, and reaction obtains 4- pyridinemethanol.
5. according to the synthetic method of 4- pyridinemethanol described in claim 3 or 4 a kind of, it is characterised in that: the hydroxide
The mass percent of potassium solution is 20%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711095592.XA CN109761889A (en) | 2017-11-09 | 2017-11-09 | A kind of synthetic method of 4- pyridinemethanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711095592.XA CN109761889A (en) | 2017-11-09 | 2017-11-09 | A kind of synthetic method of 4- pyridinemethanol |
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| Publication Number | Publication Date |
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| CN109761889A true CN109761889A (en) | 2019-05-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711095592.XA Withdrawn CN109761889A (en) | 2017-11-09 | 2017-11-09 | A kind of synthetic method of 4- pyridinemethanol |
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| Country | Link |
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| CN (1) | CN109761889A (en) |
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2017
- 2017-11-09 CN CN201711095592.XA patent/CN109761889A/en not_active Withdrawn
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Application publication date: 20190517 |
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