CN108658739A - A kind of synthetic method of intermediate 3,5- Dichloro-2-pentanones - Google Patents
A kind of synthetic method of intermediate 3,5- Dichloro-2-pentanones Download PDFInfo
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- CN108658739A CN108658739A CN201810661228.3A CN201810661228A CN108658739A CN 108658739 A CN108658739 A CN 108658739A CN 201810661228 A CN201810661228 A CN 201810661228A CN 108658739 A CN108658739 A CN 108658739A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
Abstract
The invention discloses a kind of synthetic method of 3,5 dichloro of intermediate, 2 pentanone, α acetyl group gamma butyrolactone, Anhydrous potassium carbonate, α acetyl group α chlorine gamma butyrolactone, hydrochloric acid, glacial acetic acid, Cu2O, benzidine and anhydrous THF are primary raw material, α acetyl group gamma butyrolactone is adopted under the catalytic action of one sulfonic acid chloride of lewis acid, it is converted into its corresponding enol-type structure, then the positions α of chlorine cation attack carbonyl, proton translocation then occurs, light base takes off Hydrogen Proton, by resetting, it is converted into the more stable carbonyl of structure, when the present invention is using acetic acid as solvent, there is certain dissolubility to organic phase and hydrochloric acid, reaction is easier to make for, reaction yield is greatly improved under the effect of the catalyst, shorten the prothioconazoles technological process of production, reduce energy consumption.
Description
Technical field
The present invention relates to a kind of synthetic methods of intermediate 3,5- Dichloro-2-pentanones, belong to catalysis technical field.
Background technology
3,5- Dichloro-2-pentanones are important chemical intermediate, and 3,5- Dichloro-2-pentanones need in following Chemical market
The amount of asking should be very considerable, and more considerable economic benefit can be brought by improving its selective synthesized to it with yield.Seek
One kind efficiently synthesizing 3,5- Dichloro-2-pentanone methods and is highly desirable.
Invention content
The purpose of the present invention is to provide a kind of intermediate 3, the synthetic method of 5- Dichloro-2-pentanones, this method is optimizing
Under the conditions of can be catalyzed the reaction of α-acetyl group-α-chloro- gamma-butyrolacton and hydrochloric acid, there is higher product yield.
A kind of intermediate 3, the synthetic method of 5- Dichloro-2-pentanones, this approach includes the following steps：
α-acetyl group-gamma-butyrolacton of 40g is added into the flask of 250m1 for step 1, at room temperature, opens stirring, uses ice water
Bath is cooled down, and maintains the temperature at 5 DEG C, the sulfonic acid chloride of 44.3g is slowly added dropwise；
Step 2 after being added dropwise, is gradually increased to room temperature, and the reaction was continued at room temperature, and about 6 hours will react after reaction
Liquid pours into 150m1 ice water, then stirring pours into mixed liquor in the separatory funnel of 500m1, with dichloromethane (3 × 40m1)
Organic phase is extracted, the organic phase of concentration is dried with anhydrous sodium sulfate, and organic phase concentration obtains colourless liquid α-acetyl
Base-α-chloro- gamma-butyrolacton；
Step 3, at room temperature, into the flask of 500ml, sequentially add 50.78g α-acetyl group-α-chloro- gamma-butyrolacton,
36% hydrochloric acid of 69g concentration, the glacial acetic acid and 3.0gCu of 20g2O@COF nanocatalysts, stirring, are to slowly warm up to 105 DEG C,
Solution colour is gradually deepened, and after about 5 hours of insulation reaction, stops heating, reaction solution is cooled to room temperature；
100ml water is added into flask for step 4, stirs slightly, solution is poured into the separatory funnel of 500ml and detached, and uses
Dichloromethane (3 × 30ml) aqueous phase extracted, the organic phase of concentration use the aqueous solution and water of saturated sodium bicarbonate successively
Washing, organic phase drying, concentration, Liquid Residue is evaporated under reduced pressure, and obtains weak yellow liquid 3,5- Dichloro-2-pentanones,
The Cu2O@COF nanocatalyst preparation methods are as follows：
Step 1, by 10mgCu2O, 16mg benzidine and the anhydrous THF of 1ml are added in reactor, in the oil bath that temperature is 50 DEG C
Heating 30min adds the 4ml solution dissolved with 10mg trihydroxy mesitylene formaldehyde then with the rate of addition of 0.8ml/h dropwise
Enter in reactor, reacts and continue 12h, obtain product Cu after reaction, after centrifugation2O@Polyimine；
Step 2, by Cu obtained above2The n-butanol and o-dichlorohenzene mixed solvent of O@Polyimine and 3.0ml（Volume ratio
It is 1:5）It is added in reaction tube, is put into cooling in 77k liquid nitrogen, freeze thawing deaerates three times, reacted 3 days in 120 DEG C of baking ovens after tube sealing;
After reaction, isolated product Cu2O@COF nanocatalysts.
Advantageous effect：The present invention provides a kind of intermediate 3, the synthetic method of 5- Dichloro-2-pentanones, α-acetyl group-γ-
Butyrolactone is converted into its corresponding enol-type structure under the catalytic action of one sulfonic acid chloride of lewis acid, then chlorine cation into
The positions α for attacking carbonyl, then occur proton translocation, and light base takes off Hydrogen Proton, by resetting, are converted into the more stable carbonyl of structure
Base；Decarboxylation was heated in hydrolysis, then catalysis to α-acetyl group-α-chloro- gamma-butyrolacton in acid condition before this, then alcohol hydroxyl
The displacement of base and chlorine is halogenated to obtain product, and reaction can carry out directly in concentrated hydrochloric acid, but reactant in the case of not solubilizer
Between contact with each other more difficult, reaction yield is relatively low and is easy to occur the case where reaction solution coking, but is made with acetic acid
For solvent when,
There are certain dissolubility, reaction to be easier to make for organic phase and hydrochloric acid, reaction yield obtains under the effect of the catalyst
To increasing substantially.
Specific implementation mode
Embodiment 1
A kind of intermediate 3, the synthetic method of 5- Dichloro-2-pentanones include the following steps：
α-acetyl group-gamma-butyrolacton of 40g is added into the flask of 250m1 for step 1, at room temperature, opens stirring, uses ice water
Bath is cooled down, and maintains the temperature at 5 DEG C, the sulfonic acid chloride of 44.3g is slowly added dropwise；
Step 2 after being added dropwise, is gradually increased to room temperature, and the reaction was continued at room temperature, and about 6 hours will react after reaction
Liquid pours into 150m1 ice water, then stirring pours into mixed liquor in the separatory funnel of 500m1, with dichloromethane (3 × 40m1)
Organic phase is extracted, the organic phase of concentration is dried with anhydrous sodium sulfate, and organic phase concentration obtains colourless liquid α-acetyl
Base-α-chloro- gamma-butyrolacton；
Step 3, at room temperature, into the flask of 500ml, sequentially add 50.78g α-acetyl group-α-chloro- gamma-butyrolacton,
36% hydrochloric acid of 69g concentration, the glacial acetic acid and 3.0gCu of 20g2O@COF nanocatalysts, stirring, are to slowly warm up to 105 DEG C,
Solution colour is gradually deepened, and after about 5 hours of insulation reaction, stops heating, reaction solution is cooled to room temperature；
100ml water is added into flask for step 4, and solution is poured into the separatory funnel of 500ml and detached, uses dichloro by stirring
Aqueous phase extracted, each 30ml, the organic phase of concentration use the aqueous solution and water of saturated sodium bicarbonate to methane successively three times
Washing, organic phase drying, concentration, Liquid Residue is evaporated under reduced pressure, and obtains weak yellow liquid 3,5- Dichloro-2-pentanones,
The Cu2O@COF nanocatalyst preparation methods are as follows：
Step 1, by 10mgCu2O, 16mg benzidine and the anhydrous THF of 1ml are added in reactor, in the oil bath that temperature is 50 DEG C
Heating 30min adds the 4ml solution dissolved with 10mg trihydroxy mesitylene formaldehyde then with the rate of addition of 0.8ml/h dropwise
Enter in reactor, reacts and continue 12h, obtain product Cu after reaction, after centrifugation2O@Polyimine；
Step 2, by Cu obtained above2The n-butanol and o-dichlorohenzene mixed solvent of O@Polyimine and 3.0ml（Volume ratio
It is 1:5）It is added in reaction tube, is put into cooling in 77k liquid nitrogen, freeze thawing deaerates three times, reacted 3 days in 120 DEG C of baking ovens after tube sealing;
After reaction, isolated product Cu2O@COF nanocatalysts.
Embodiment 2
Step 3, at room temperature, into the flask of 500ml, sequentially add 50.78g α-acetyl group-α-chloro- gamma-butyrolacton,
36% hydrochloric acid of 34.5g concentration, the glacial acetic acid and 3.0gCu of 20g2O@COF nanocatalysts, stirring, are to slowly warm up to 105
DEG C, solution colour is gradually deepened, and after about 5 hours of insulation reaction, stops heating, reaction solution is cooled to room temperature；Remaining step
With embodiment 1.
Embodiment 3
Step 3, at room temperature, into the flask of 500ml, sequentially add 50.78g α-acetyl group-α-chloro- gamma-butyrolacton,
36% hydrochloric acid of 17.3g concentration, the glacial acetic acid and 3.0gCu of 20g2O@COF nanocatalysts, stirring, are to slowly warm up to 105
DEG C, solution colour is gradually deepened, and after about 5 hours of insulation reaction, stops heating, reaction solution is cooled to room temperature；Remaining step
With embodiment 1.
Embodiment 4
Step 3, at room temperature, into the flask of 500ml, sequentially add 50.78g α-acetyl group-α-chloro- gamma-butyrolacton,
36% hydrochloric acid of 8.6g concentration, the glacial acetic acid and 3.0gCu of 20g2O@COF nanocatalysts, stirring, are to slowly warm up to 105 DEG C,
Solution colour is gradually deepened, and after about 5 hours of insulation reaction, stops heating, reaction solution is cooled to room temperature；Remaining step is the same as real
Apply example 1.
Embodiment 5
Step 3, at room temperature, into the flask of 500ml, sequentially add 50.78g α-acetyl group-α-chloro- gamma-butyrolacton,
36% hydrochloric acid of 69g concentration, the glacial acetic acid and 3.0gCu of 20g2O@COF nanocatalysts, stirring, are to slowly warm up to 105 DEG C,
Solution colour is gradually deepened, and after about 5 hours of insulation reaction, stops heating, reaction solution is cooled to room temperature；Remaining step is the same as real
Apply example 1.
Embodiment 6
Step 3, at room temperature, into the flask of 500ml, sequentially add 50.78g α-acetyl group-α-chloro- gamma-butyrolacton,
36% hydrochloric acid of 4.3g concentration, the glacial acetic acid and 3.0gCu of 20g2O@COF nanocatalysts, stirring, are to slowly warm up to 105 DEG C,
Solution colour is gradually deepened, and after about 5 hours of insulation reaction, stops heating, reaction solution is cooled to room temperature；Remaining step is the same as real
Apply example 1.
Embodiment 7
Step 3, at room temperature, into the flask of 500ml, sequentially add 50.78g α-acetyl group-α-chloro- gamma-butyrolacton,
36% hydrochloric acid of 86.3g concentration, the glacial acetic acid and 3.0gCu of 20g2O@COF nanocatalysts, stirring, are to slowly warm up to 105
DEG C, solution colour is gradually deepened, and after about 5 hours of insulation reaction, stops heating, reaction solution is cooled to room temperature；Remaining step
With embodiment 1.
Embodiment 8
Step 3, at room temperature, into the flask of 500ml, sequentially add 50.78g α-acetyl group-α-chloro- gamma-butyrolacton,
36% hydrochloric acid of 103.6g concentration, the glacial acetic acid and 3.0gCu of 20g2O@COF nanocatalysts, stirring, are to slowly warm up to 105
DEG C, solution colour is gradually deepened, and after about 5 hours of insulation reaction, stops heating, reaction solution is cooled to room temperature；Remaining step
With embodiment 1.
Embodiment 9
Step 3, at room temperature, into the flask of 500ml, sequentially add 50.78g α-acetyl group-α-chloro- gamma-butyrolacton,
36% hydrochloric acid of 120.9g concentration, the glacial acetic acid and 3.0gCu of 20g2O@COF nanocatalysts, stirring, are to slowly warm up to 105
DEG C, solution colour is gradually deepened, and after about 5 hours of insulation reaction, stops heating, reaction solution is cooled to room temperature；Remaining step
With embodiment 1.
Embodiment 10
Step 3, at room temperature, into the flask of 500ml, sequentially add 50.78g α-acetyl group-α-chloro- gamma-butyrolacton,
36% hydrochloric acid of 138.2g concentration, the glacial acetic acid and 3.0gCu of 20g2O@COF nanocatalysts, stirring, are to slowly warm up to 105
DEG C, solution colour is gradually deepened, and after about 5 hours of insulation reaction, stops heating, reaction solution is cooled to room temperature；Remaining step
With embodiment 1.
Reference examples 1
It is with 1 difference of embodiment：In the synthesis step 1 of intermediate, replace sulfonic acid chloride, remaining step and embodiment with chlorine
1 is identical.
Reference examples 2
It is with 1 difference of embodiment：In the synthesis step 1 of intermediate, replace sulfonic acid chloride, remaining step and reality with thionyl chloride
It is identical to apply example 1.
Reference examples 3
It is with 1 difference of embodiment：In the synthesis step 1 of intermediate, α-acetyl group-gamma-butyrolacton, sulfonic acid chloride mass ratio are
10:1, remaining step is identical with embodiment 1.
Reference examples 4
It is with 1 difference of embodiment：In the synthesis step 1 of intermediate, α-acetyl group-gamma-butyrolacton, sulfonic acid chloride mass ratio are
1:10, remaining step is identical with embodiment 1.
Reference examples 5
It is with 1 difference of embodiment：In the synthesis step 3 of intermediate, glacial acetic acid is not added, remaining step and embodiment 1
It is identical.
Reference examples 6
It is with 1 difference of embodiment：In the synthesis step 3 of intermediate, replace glacial acetic acid, remaining step with the ethylene glycol of equivalent
It is identical with embodiment 1.
Reference examples 7
It is with 1 difference of embodiment：In the synthesis step 3 of intermediate, Cu is used2O replaces Cu2O@COF catalysis；Remaining step with
Embodiment 1 is identical.
Reference examples 8
It is with 1 difference of embodiment：In the synthesis step 3 of intermediate, catalyst is not added；Remaining step and embodiment 1
It is identical.
Reference examples 9
It is with 1 difference of embodiment：In the synthesis step 1 of catalyst, Cu2O, benzidine mass ratio is 1:5, remaining step with
Embodiment 1 is identical.
Reference examples 10
It is with 1 difference of embodiment：In the synthesis step 1 of catalyst, Cu2O, benzidine mass ratio is 5:1, remaining step with
Embodiment 1 is identical.
It is as shown in the table for reaction result under embodiment and reference examples different condition
The experimental results showed that catalyst imitates α-acetyl group-α-chloro- gamma-butyrolacton and hydrochloric acid synthetic reaction with good catalysis
Fruit, in one timing of reaction condition, intermediate yield is higher, and catalytic performance is better, otherwise poorer；Chloro- γ-the fourths of α-acetyl group-α-
Lactone, concentrated hydrochloric acid mass ratio are 5：7 and 10:When 7（That is embodiment 1,2）, other dispensings fix, and synthetic effect is preferably up to
97.5%, with embodiment 1 the difference lies in that embodiment 3 to embodiment 10 changes primary raw material α-acetyl group-α-chloro- γ-respectively
The dosage and proportioning of butyrolactone, concentrated hydrochloric acid, have the yield of synthetic product different influences；Reference examples 1 to reference examples 2 use chlorine
Replace sulfonic acid chloride with thionyl chloride, other steps are identical, and product yield is caused to be substantially reduced, and illustrate sulfonic acid chloride to reaction
Yield influences very big；Reference examples 3 to reference examples 4 change α-acetyl group-gamma-butyrolacton, sulfonic acid chloride mass ratio, and effect is still not
It is good, illustrate that the dosage of sulfonic acid chloride is preferable in the interior effect of certain proportioning；Reference examples 5 to 6 spent glycol of reference examples substitution glacial acetic acid is made
For reaction dissolvent so that product obtains yield reduction, and reaction effect is obviously deteriorated, and it is very big to illustrate that weakly acidic solvent influences reaction；It is right
It 7 being not added with catalyst as usual to reference examples 8 and replaces catalyst with cuprous oxide, the conversion ratio and selectivity of reaction are very low,
Reaction effect is obviously deteriorated, and product yield is not still high；Reference examples 9 are to reference examples 10Cu2O, benzidine mass ratio changes,
The activity change of catalyst, reaction effect are unsatisfactory；Therefore 3,5- Dichloro-2-pentanones are synthesized using the catalyst of the present invention
Reaction has excellent catalytic effect.
Claims (2)
1. a kind of intermediate 3, the synthetic method of 5- Dichloro-2-pentanones, it is characterised in that this approach includes the following steps：
Step 1, at room temperature, the α-acetyl group-gamma-butyrolacton being added into flask are opened stirring, are carried out with ice-water bath cold
But, 5 DEG C are maintained the temperature at, the sulfonic acid chloride being slowly added dropwise；
Step 2 after being added dropwise, is gradually increased to room temperature, and the reaction was continued at room temperature, and about 6 hours will react after reaction
Liquid pours into ice water, and then mixed liquor is poured into the separatory funnel of 500m1, organic phase is extracted with dichloromethane by stirring, collect
In organic phase be dried with anhydrous sodium sulfate, organic phase concentration, obtain colourless liquid α-acetyl group-α-chloro- γ-Ding Nei
Ester；
Step 3, at room temperature sequentially adds α-acetyl group-α-chloro- gamma-butyrolacton, concentration 36% into the flask of 500ml
Hydrochloric acid, glacial acetic acid and Cu2O@COF nanocatalysts, stirring, are to slowly warm up to 105 DEG C, and solution colour is gradually deepened, heat preservation
After reacting about 5 hours, stops heating, reaction solution is cooled to room temperature；
100ml water is added into flask for step 4, stirs slightly, solution is poured into the separatory funnel of 500ml and detached, and uses
Dichloromethane aqueous phase extracted, the organic phase of concentration use the aqueous solution and water of saturated sodium bicarbonate successively
Washing, organic phase drying, concentration, Liquid Residue are evaporated under reduced pressure, and weak yellow liquid 3,5- Dichloro-2-pentanones are obtained.
2. a kind of intermediate 3 according to claim 1, the synthetic method of 5- Dichloro-2-pentanones, which is characterized in that
The Cu2O@COF nanocatalyst preparation methods are as follows：
Step 1, by 10mgCu2O, 16mg benzidine and the anhydrous THF of 1ml are added in reactor, add in the oil bath that temperature is 50 DEG C
The 4ml solution dissolved with 10mg trihydroxy mesitylene formaldehyde is added dropwise then with the rate of addition of 0.8ml/h by hot 30min
In reactor, reacts and continue 12h, obtain product Cu after reaction, after centrifugation2O@Polyimine；
Step 2, by Cu obtained above2The n-butanol and o-dichlorohenzene mixed solvent of O@Polyimine and 3.0ml（Volume ratio is
1:5）It is added in reaction tube, is put into cooling in 77k liquid nitrogen, freeze thawing deaerates three times, reacted 3 days in 120 DEG C of baking ovens after tube sealing;Instead
After answering, isolated product Cu2O@COF nanocatalysts.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113831229A (en) * | 2021-09-26 | 2021-12-24 | 浙江新和成股份有限公司 | Green synthesis method of vitamin B1 intermediate |
| CN114685253A (en) * | 2020-12-30 | 2022-07-01 | 南通泰禾化工股份有限公司 | Preparation method of prothioconazole intermediate 3, 5-dichloro-2-pentanone |
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| CN104292089A (en) * | 2014-09-30 | 2015-01-21 | 大连九信生物化工科技有限公司 | Synthetic process of 1-chloro-cyclopropanecarbonyl chloride |
| CN107473949A (en) * | 2017-09-26 | 2017-12-15 | 安徽国星生物化学有限公司 | A kind of synthesis technique of the pentanone of 3,5 dichloro 2 |
| CN107824221A (en) * | 2017-12-01 | 2018-03-23 | 江苏师范大学 | A kind of preparation method for nitrogen oxides photochemical catalyst of degrading |
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2018
- 2018-06-25 CN CN201810661228.3A patent/CN108658739A/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104292089A (en) * | 2014-09-30 | 2015-01-21 | 大连九信生物化工科技有限公司 | Synthetic process of 1-chloro-cyclopropanecarbonyl chloride |
| CN104292089B (en) * | 2014-09-30 | 2016-01-13 | 大连九信生物化工科技有限公司 | The synthesis technique of the chloro-1 '-chloracetyl cyclopropane of a kind of 1- |
| CN107473949A (en) * | 2017-09-26 | 2017-12-15 | 安徽国星生物化学有限公司 | A kind of synthesis technique of the pentanone of 3,5 dichloro 2 |
| CN107824221A (en) * | 2017-12-01 | 2018-03-23 | 江苏师范大学 | A kind of preparation method for nitrogen oxides photochemical catalyst of degrading |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114685253A (en) * | 2020-12-30 | 2022-07-01 | 南通泰禾化工股份有限公司 | Preparation method of prothioconazole intermediate 3, 5-dichloro-2-pentanone |
| CN113831229A (en) * | 2021-09-26 | 2021-12-24 | 浙江新和成股份有限公司 | Green synthesis method of vitamin B1 intermediate |
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Application publication date: 20181016 |