CN108586202A - A kind of synthetic method of intermediate 4- phenylbutanols - Google Patents
A kind of synthetic method of intermediate 4- phenylbutanols Download PDFInfo
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- CN108586202A CN108586202A CN201810733661.3A CN201810733661A CN108586202A CN 108586202 A CN108586202 A CN 108586202A CN 201810733661 A CN201810733661 A CN 201810733661A CN 108586202 A CN108586202 A CN 108586202A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
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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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
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Abstract
The invention discloses a kind of synthetic method of 4 phenylbutanol of intermediate, ferrous sulfate, I2、NaBH4, Fe N/C, four pyridine azophenlyene and 4 phenylbutyric acids be primary raw material, it is raw materials used according to the following ratio：4 phenylbutyric acids, I2Mass ratio is 5：4；Fe‑N/C、NaBH4Mass ratio is 5：8；Four pyridine azophenlyene, ferrous sulfate molar ratio are 5：7；The synthesis technology of the present invention obtains 4 phenylbutanols under the action of catalyst Fe N/C using the sodium borohydride system of 4 phenylbutyric acids and iodine by reduction reaction, compared to traditional synthetic method, the easily separated recycling of catalyst, through a large number of experiments, continue to optimize the temperature of experiment, dosage, proportioning and technological process so that the operation is convenient, time is short, and the yield of product and purity are largely increased.
Description
Technical field
The present invention relates to a kind of synthetic methods of intermediate 4- phenylbutanols, belong to chemical industry synthesis field.
Background technology
4- phenylbutanols（4-phenylbutanol）CAS：3360-41-6 is synthesis 4-（4- phenylbutoxies）Benzoic acid
Important chemical intermediate is long-acting beta2Receptor stimulating agent salmeterol（salmeterol）Intermediate, it can also be used to synthesize
Caffeic acid benzene butyl alcohol ester with anti-tumor activity etc..Synthetic method is more, and preferable method has：Benzene and succinic anhydride are through Fu Ke
React 4- oxos -4-phenylbutyrate finally uses LiAlH through zinc-amalgam reduction carbonyl4Reduction carboxyl obtains；After there is method to change
Into through Wolff-Kishner reduction, esterification and NaBH4It restores；4-phenylbutyrate is through esterification, NaBH4Restore or pass through
Aromatic series reductase bioconversion obtains.It is that raw material is made through one step of Friedel-Crafts reaction with benzene and gamma-butyrolacton, by aluminium chloride after reaction
It is all dissolved in buck with product, precipitation product is neutralized with acid again after separating benzene layer, needs to be evaporated under reduced pressure obtained sterling；Reaction conversion
Rate is relatively low, and post-processing step is complex, and the yield and purity of product be not high, limits its industrial applications and exploitation, therefore
There is an urgent need for invent a kind of processing step simple, product yield and the higher synthetic methods of purity.
Invention content
The purpose of the present invention is to provide a kind of synthetic methods of intermediate 4- phenylbutanols, and this method is with optimal conditions
It can be catalyzed the reduction reaction of 4-phenylbutyrate, there is higher product yield.
1, a kind of synthetic method of intermediate 4- phenylbutanols, it is characterised in that this approach includes the following steps：
0.5g Fe-N/C catalyst 0.8g NaBH are added in step 1 in 250m1 four-hole boiling flasks4With 30ml tetrahydrofurans, machinery
Stirring is slowly heated to 60 DEG C, keeps the temperature 15min；
3.0g 4-phenylbutyrates are added to above-mentioned system in step 2, and isothermal reaction 15min, is added dropwise 10ml 2.4g at this temperature
I2Tetrahydrofuran solution, system is gradually creamy white, and a large amount of bubbles of output, insulation reaction 5h；
Step 3, the reaction was complete afterwards with the stopped reaction of the HCl of 5m1 3mol/L, and upper layer yellow organic liquor, lower layer's white are solid at this time
Residual reaction liquid is poured into single-necked flask by body after stirring 15min, in orange after revolving removing tetrahydrofuran；
Step 4 after the dissolving of 30ml dichloromethane is added, filters to obtain pale yellow filtrate, uses saturated salt solution and deionized water successively
It washs, removes iodine with anhydrous calcium chloride water removal and a small amount of sodium thiosulfate under the conditions of magnetic agitation, obtain water white transparency organic liquor, rotate
Except solvent, light yellow transparent liquid 4- phenylbutanols are obtained.
The Fe-N/C method for preparing catalyst is as follows：
Step 1, by tetra- pyridine azophenlyene ultrasonic disperses of 0.25mmol in 25mlN, dinethylformamide solvent, be named as solution
A；
Step 2,0.35mmol ferrous sulfate are dissolved in 10m1N, in dinethylformamide solvent, referred to as solution B；
Step 3, under strong stirring, solution B is slowly dropped in solution A, 15min is added dropwise that form red mixing molten
Liquid；
Step 4 after being stirred for 30min, is transferred to 160 DEG C of reaction 12h in baking oven, is then centrifuged for detaching, be washed with dichloromethane
Three times, 60 DEG C of vacuum drying for 24 hours, obtain red predecessor powder sample；
Precursor Powder object after drying is placed in tube furnace, hydrogen atmosphere, respectively 600,650,700 and 750 by step 5
1h, 30 DEG C/min of the rate of heat addition are calcined under the conditions of DEG C；
Sample after step 6, pyrolysis is after 6M hydrochloric acid handles 24 h under the conditions of 45 DEG C, distillation water washing to neutrality, 60 DEG C
It is dried in vacuo a night, obtains Fe-N/C catalyst.
Advantageous effect：The present invention provides a kind of synthetic method of intermediate 4- phenylbutanols, the boron hydrogen of 4-phenylbutyrate and iodine
Change sodium system and obtains 4- phenylbutanols by reduction reaction under the action of catalyst Fe-N/C.Four pyridine azophenlyene（tpphz）Molecule
Middle high-content stablize must nitrogen-atoms component can promote the Fe-N active sites of high temperature pyrolysis process nitrogen functional group and high concentration
Formation；There is the single precursor Fe-tpphz of smart design unique design feature, rule to be distributed Fe-N coordination centers, can be with
Effectively hinder the aggregation of the iron species in subsequent carbonisation；It is auto-dope catalyst precursor that Fe-tpphz complex compounds, which are applied,
Completely eliminate the use of external carrier.Strong interaction can be built between the catalyst active component of generation, to increase
The catalytic activity and durability of powerful catalyst.In addition, abundant nanoaperture can facilitate the diffusion and transport of reaction species.It is logical
A large amount of experiment is crossed, the temperature of experiment, dosage, proportioning and technological process are continued to optimize so that the operation is convenient, the time
It is short, and the yield of product and purity are largely increased.
Specific implementation mode
Embodiment 1
1, a kind of synthetic method of intermediate 4- phenylbutanols, it is characterised in that this approach includes the following steps：
0.5g Fe-N/C catalyst 0.8g NaBH are added in step 1 in 250m1 four-hole boiling flasks4With 30ml tetrahydrofurans, machinery
Stirring is slowly heated to 60 DEG C, keeps the temperature 15min；
3.0g 4-phenylbutyrates are added to above-mentioned system in step 2, and isothermal reaction 15min, is added dropwise 10ml 2.4g at this temperature
I2Tetrahydrofuran solution, system is gradually creamy white, and a large amount of bubbles of output, insulation reaction 5h；
Step 3, the reaction was complete afterwards with the stopped reaction of the HCl of 5m1 3mol/L, and upper layer yellow organic liquor, lower layer's white are solid at this time
Residual reaction liquid is poured into single-necked flask by body after stirring 15min, in orange after revolving removing tetrahydrofuran；
Step 4 after the dissolving of 30ml dichloromethane is added, filters to obtain pale yellow filtrate, uses saturated salt solution and deionized water successively
It washs, removes iodine with anhydrous calcium chloride water removal and a small amount of sodium thiosulfate under the conditions of magnetic agitation, obtain water white transparency organic liquor, rotate
Except solvent, light yellow transparent liquid 4- phenylbutanols are obtained.
The Fe-N/C method for preparing catalyst is as follows：
Step 1, by tetra- pyridine azophenlyene ultrasonic disperses of 0.25mmol in 25mlN, dinethylformamide solvent, be named as solution
A；
Step 2,0.35mmol ferrous sulfate are dissolved in 10m1N, in dinethylformamide solvent, referred to as solution B；
Step 3, under strong stirring, solution B is slowly dropped in solution A, 15min is added dropwise that form red mixing molten
Liquid；
Step 4 after being stirred for 30min, is transferred to 160 DEG C of reaction 12h in baking oven, is then centrifuged for detaching, be washed with dichloromethane
Three times, 60 DEG C of vacuum drying for 24 hours, obtain red predecessor powder sample；
Precursor Powder object after drying is placed in tube furnace, hydrogen atmosphere, respectively 600,650,700 and 750 by step 5
1h, 30 DEG C/min of the rate of heat addition are calcined under the conditions of DEG C；
Sample after step 6, pyrolysis is after 6M hydrochloric acid handles 24 h under the conditions of 45 DEG C, distillation water washing to neutrality, 60 DEG C
It is dried in vacuo a night, obtains Fe-N/C catalyst.
Embodiment 2
2.0g 4-phenylbutyrates are added to above-mentioned system in step 2, and isothermal reaction 15min, is added dropwise 10ml 2.4g at this temperature
I2Tetrahydrofuran solution, system is gradually creamy white, and a large amount of bubbles of output, insulation reaction 5h；The same embodiment of remaining step
1。
Embodiment 3
1.0g 4-phenylbutyrates are added to above-mentioned system in step 2, and isothermal reaction 15min, is added dropwise 10ml 2.4g at this temperature
I2Tetrahydrofuran solution, system is gradually creamy white, and a large amount of bubbles of output, insulation reaction 5h；The same embodiment of remaining step
1。
Embodiment 4
4.0g 4-phenylbutyrates are added to above-mentioned system in step 2, and isothermal reaction 15min, is added dropwise 10ml 2.4g at this temperature
I2Tetrahydrofuran solution, system is gradually creamy white, and a large amount of bubbles of output, insulation reaction 5h；The same embodiment of remaining step
1。
Embodiment 5
5.0g 4-phenylbutyrates are added to above-mentioned system in step 2, and isothermal reaction 15min, is added dropwise 10ml 2.4g at this temperature
I2Tetrahydrofuran solution, system is gradually creamy white, and a large amount of bubbles of output, insulation reaction 5h；The same embodiment of remaining step
1。
Embodiment 6
6.0g 4-phenylbutyrates are added to above-mentioned system in step 2, and isothermal reaction 15min, is added dropwise 10ml 2.4g at this temperature
I2Tetrahydrofuran solution, system is gradually creamy white, and a large amount of bubbles of output, insulation reaction 5h；The same embodiment of remaining step
1。
Embodiment 7
7.0g 4-phenylbutyrates are added to above-mentioned system in step 2, and isothermal reaction 15min, is added dropwise 10ml 2.4g at this temperature
I2Tetrahydrofuran solution, system is gradually creamy white, and a large amount of bubbles of output, insulation reaction 5h；The same embodiment of remaining step
1。
Embodiment 8
8.0g 4-phenylbutyrates are added to above-mentioned system in step 2, and isothermal reaction 15min, is added dropwise 10ml 2.4g at this temperature
I2Tetrahydrofuran solution, system is gradually creamy white, and a large amount of bubbles of output, insulation reaction 5h；The same embodiment of remaining step
1。
Embodiment 9
9.0g 4-phenylbutyrates are added to above-mentioned system in step 2, and isothermal reaction 15min, is added dropwise 10ml 2.4g at this temperature
I2Tetrahydrofuran solution, system is gradually creamy white, and a large amount of bubbles of output, insulation reaction 5h；The same embodiment of remaining step
1。
Embodiment 10
10.0g 4-phenylbutyrates are added to above-mentioned system in step 2, and isothermal reaction 15min, is added dropwise 10ml at this temperature
2.4g I2Tetrahydrofuran solution, system is gradually creamy white, and a large amount of bubbles of output, insulation reaction 5h；Remaining step is the same as real
Apply example 1.
Reference examples 1
It is with 1 difference of embodiment：In the synthesis step 1 of intermediate, with the Fe of equivalent3O4As catalyst, remaining step
It is identical with embodiment 1.
Reference examples 2
It is with 1 difference of embodiment：In the synthesis step 1 of intermediate, catalyst Fe-N/C is not added, remaining step and reality
It is identical to apply example 1.
Reference examples 3
It is with 1 difference of embodiment：In the synthesis step 1 of catalyst, four pyridine azophenlyene, remaining step and implementation are not added
Example 1 is identical.
Reference examples 4
It is with 1 difference of embodiment：In the synthesis step 1 of catalyst, replace four pyridine azophenlyene with the pyridine of equivalent, remaining step
Suddenly identical with embodiment 1.
Reference examples 5
It is with 1 difference of embodiment：In the synthesis step 2 of catalyst, four pyridine azophenlyene, ferrous sulfate molar ratio are 7：5,
Remaining step is identical with embodiment 1.
Reference examples 6
It is with 1 difference of embodiment：In the synthesis step 2 of catalyst, four pyridine azophenlyene, ferrous sulfate molar ratio are 1：1,
Remaining step is identical with embodiment 1.
Reference examples 7
It is with 1 difference of embodiment：In the synthesis step 5 of catalyst, calcined under carbon dioxide atmosphere；Remaining step and reality
It is identical to apply example 1.
Reference examples 8
It is with 1 difference of embodiment：In the synthesis step 5 of catalyst, calcine in a nitrogen atmosphere；Remaining step and embodiment
1 is identical.
Reference examples 9
It is with 1 difference of embodiment：In the synthesis step 6 of catalyst, no longer with HCl treatment be pyrolyzed sample, remaining step with
Embodiment 1 is identical.
Reference examples 10
It is with 1 difference of embodiment：In the synthesis step 6 of catalyst, it is pyrolyzed sample with the naoh treatment of isoconcentration,
Remaining step is identical with embodiment 1.
It is as shown in the table for reaction result under embodiment and reference examples different condition
| 4- phenylbutanols yield/% | |
| Embodiment 1 | 99.0 |
| Embodiment 2 | 75.1 |
| Embodiment 3 | 69.1 |
| Embodiment 4 | 76.6 |
| Embodiment 5 | 80.0 |
| Embodiment 6 | 64.5 |
| Embodiment 7 | 56.3 |
| Embodiment 8 | 64.0 |
| Embodiment 9 | 59.6 |
| Embodiment 10 | 60.7 |
| Reference examples 1 | 45.7 |
| Reference examples 2 | 39.4 |
| Reference examples 3 | 43.5 |
| Reference examples 4 | 51.2 |
| Reference examples 5 | 58.1 |
| Reference examples 6 | 60.6 |
| Reference examples 7 | 44.0 |
| Reference examples 8 | 40.1 |
| Reference examples 9 | 49.6 |
| Reference examples 10 | 53.5 |
The experimental results showed that catalyst has good catalytic effect to the reduction reaction of 4-phenylbutyrate, it is certain in reaction condition
When, intermediate yield is higher, and catalytic performance is better, otherwise poorer；4-phenylbutyrate, I2Mass ratio is 5：When 4, other dispensings are solid
Fixed, synthetic effect is best, with embodiment 1 the difference lies in that embodiment 2 changes primary raw material 4- phenyl fourths to embodiment 10 respectively
Acid, I2Dosage and proportioning, in spite of certain effect, but be not so good as 1 high income of embodiment；Reference examples 1 no longer add to reference examples 2
Enter catalyst Fe-N/C and uses Fe3O4Substitution, other steps are identical, and product yield is caused to be substantially reduced, and illustrate composite catalyzing
Agent influences the product of reaction very big；Reference examples 3 to reference examples 4 do not add four pyridine azophenlyene and are replaced with pyridine, effect according to
It is so bad, illustrate that four pyridine azophenlyene are essential ingredients in catalyst synthesis；Reference examples 5 to reference examples 6 change four pyridines
Azophenlyene, ferrous sulfate molar ratio, catalytic effect are obviously deteriorated, and illustrate being affected with comparison catalytic performance for the two；Reference examples 7
It is calcined under nitrogen and carbon dioxide atmosphere respectively to reference examples 8, is catalyzed the variation with obvious effects of reaction, illustrates hydrogen atmosphere pair
Catalyst calcination effect is preferable；Reference examples 9 are no longer handled with acid to reference examples 10 and carry out alkali process, catalyst with sodium hydroxide
Activity change, reaction effect is obviously deteriorated, and product yield is substantially reduced；Therefore using the catalyst of the present invention to centre
The synthetic reaction of body 4- phenylbutanols has excellent catalytic effect.
Claims (2)
1. a kind of synthetic method of intermediate 4- phenylbutanols, it is characterised in that this approach includes the following steps：
0.5g Fe-N/C catalyst 0.8g NaBH are added in step 1 in 250m1 four-hole boiling flasks4With 30ml tetrahydrofurans, machinery
Stirring is slowly heated to 60 DEG C, keeps the temperature 15min；
3.0g 4-phenylbutyrates are added to above-mentioned system in step 2, and isothermal reaction 15min, is added dropwise 10ml 2.4g at this temperature
I2Tetrahydrofuran solution, system is gradually creamy white, and a large amount of bubbles of output, insulation reaction 5h；
Step 3, the reaction was complete afterwards with the stopped reaction of the HCl of 5m1 3mol/L, and upper layer yellow organic liquor, lower layer's white are solid at this time
Residual reaction liquid is poured into single-necked flask by body after stirring 15min, in orange after revolving removing tetrahydrofuran；
Step 4 after the dissolving of 30ml dichloromethane is added, filters to obtain pale yellow filtrate, uses saturated salt solution and deionized water successively
It washs, removes iodine with anhydrous calcium chloride water removal and a small amount of sodium thiosulfate under the conditions of magnetic agitation, obtain water white transparency organic liquor, rotate
Except solvent, light yellow transparent liquid 4- phenylbutanols are obtained.
2. a kind of synthetic method of intermediate 4- phenylbutanols according to claim 1, which is characterized in that
The Fe-N/C method for preparing catalyst is as follows：
Step 1, by tetra- pyridine azophenlyene ultrasonic disperses of 0.25mmol in 25mlN, dinethylformamide solvent, be named as solution
A；
Step 2,0.35mmol ferrous sulfate are dissolved in 10m1N, in dinethylformamide solvent, referred to as solution B；
Step 3, under strong stirring, solution B is slowly dropped in solution A, 15min is added dropwise that form red mixing molten
Liquid；
Step 4 after being stirred for 30min, is transferred to 160 DEG C of reaction 12h in baking oven, is then centrifuged for detaching, be washed with dichloromethane
Three times, 60 DEG C of vacuum drying for 24 hours, obtain red predecessor powder sample；
Precursor Powder object after drying is placed in tube furnace, hydrogen atmosphere, respectively 600,650,700 and 750 by step 5
1h, 30 DEG C/min of the rate of heat addition are calcined under the conditions of DEG C；
Sample after step 6, pyrolysis is after 6M hydrochloric acid handles 24 h under the conditions of 45 DEG C, distillation water washing to neutrality, 60 DEG C
It is dried in vacuo a night, obtains Fe-N/C catalyst.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114162953A (en) * | 2022-01-10 | 2022-03-11 | 西安交通大学 | Sulfurized chelated zero-valent iron and preparation method and application thereof |
-
2018
- 2018-07-06 CN CN201810733661.3A patent/CN108586202B/en active Active
Non-Patent Citations (3)
| Title |
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| BETTINA HÖLZER ET AL: ""Kumada-Corriu coupling of Grignard reagents,probed with a chiral Grignard reagent"", 《CHEMICAL COMMUNICATIONS (CAMBRIDGE, UNITED KINGDOM)》 * |
| 杨正坤: ""Fe-N/C氧还原电催化剂的设计制备"", 《中国博士学位论文全文数据库，工程科技Ⅰ辑》 * |
| 陈华奇等: ""4-苯基丁醇的制备"", 《中国医药工业杂志》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114162953A (en) * | 2022-01-10 | 2022-03-11 | 西安交通大学 | Sulfurized chelated zero-valent iron and preparation method and application thereof |
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