CN105801420A - Synthetic method of 4,4-bis(2-methoxy benzoyloxy)biphenyl - Google Patents
Synthetic method of 4,4-bis(2-methoxy benzoyloxy)biphenyl Download PDFInfo
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- CN105801420A CN105801420A CN201610200241.XA CN201610200241A CN105801420A CN 105801420 A CN105801420 A CN 105801420A CN 201610200241 A CN201610200241 A CN 201610200241A CN 105801420 A CN105801420 A CN 105801420A
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- biphenyl
- stirring mixing
- 15min
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- deionized water
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/02—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of halogen
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a synthetic method of 4,4-bis(2-methoxy benzoyloxy)biphenyl, and belongs to the field of chemical synthesis.The method comprises the steps that 4,4-dibromobiphenyl, sodium hydroxide, copper sulfate pentahydrate and deionized water are stirred, mixed and heated to be reacted, then, filtration is performed, a filtrate is collected, sulfuric acid is dropwise added, washing and drying are performed, dimethyl formamide and o-Anisaldehyde are added, stirring, heat preservation and a reaction are performed, and therefore the 4,4-bis(2-methoxy benzoyloxy)biphenyl is obtained.
Description
Technical field
The present invention relates to a kind of 4, the synthetic method of double (2-methoxybenzoic acid base) biphenyl of 4-, belong to chemical industry synthesis
Field.
Background technology
4,4-double (2-methoxybenzoic acid base) biphenyl are organic chemical industry's intermediate, are widely used in synthesis medicine
And pesticide, purposes is quite varied, has dozens of kind with the fluorescent whitening agent of its synthesis, the disinfecting of manufacture
Agent has the function of uniqueness, is a kind of rising sterilization, pesticide intermediate, but 4,4-double (2-methoxies
Yl benzoic acid base) biphenyl never has comparatively ideal industrial process.Double (the 2-methoxybenzene of traditional mode of production 4,4-
Formyl) biphenyl technique backwardness, long flow path, yield is low, quantity of three wastes is big, it is difficult to administer.
Summary of the invention
The invention provides double (2-methoxybenzoic acid base) biphenyl of 4,4-that a kind of reaction condition is gentle, yield is high
Synthetic method.
For reaching above-mentioned purpose, the 4 of the present invention, the conjunction of the synthetic method of double (2-methoxybenzoic acid base) biphenyl of 4-
One-tenth route is:
In order to solve above-mentioned technical problem, the technical solution adopted in the present invention is:
(1) 4,4-'-dibromobiphenyl and 32～35mL mass concentrations by 17～18g are the sodium hydroxide solution of 15%
Stirring mixing, be placed in the autoclave of 1L, until its stirring mixing 10～15min after, continue add 90～
The copper sulphate pentahydrate of 100mg and the deionized water of 600～610mL, at 20～30 DEG C stirring mixing 10～
15min；
(2) to be mixed complete after, its intensification is heated to 250～280 DEG C so that it is reaction 4～5h, treat that it reacts
After completing so that it is stand and be cooled to 20～30 DEG C, collect yellow reaction liquid and to its sucking filtration, collect filtrate also
It being slowly added dropwise the sulfuric acid solution that mass concentration is 10%, treats that white precipitate slowly separates out, measuring its pH is
When 3～4, stop dropping sulphuric acid and be allowed to rest for precipitating 20～30min；
(3) after standing completes, to its sucking filtration and collect filter cake, with deionized water to its drip washing to filtrate pH it is
7.0, it is subsequently placed in 60～80 DEG C of baking ovens and is dried 6～8h, be prepared into 4,4 ' dihydroxybiphenyls, will
It is placed in 50～60 DEG C of baking ovens, kept dry；
(4) in the there-necked flask of 100mL, dimethylformamide 4.5～5.0g above-mentioned of 50～55mL is added
4,4 ' dihydroxybiphenyls of preparation and the o-methoxybenzaldehyde of 2.7～3.0g, make it at 60～65 DEG C
Stirring mixing 10～15min；
(5) to be mixed complete after, continue add 4.5～5.0g the sodium methoxide solution that mass concentration is 30%, treat
After there is greenish yellow solid in it, insulation reaction 30～40min, stop heating subsequently and place reaction liquid into frozen water
In, it stirred and filters, collecting filtering residue and be placed at 60～80 DEG C being dried 6～8h, 4,4-can be prepared into
Double (2-methoxybenzoic acid base) biphenyl.
Specific embodiments
4,4-'-dibromobiphenyl and 32～35mL mass concentrations by 17～18g are the sodium hydroxide solution of 15%
Stirring mixing, be placed in the autoclave of 1L, until its stirring mixing 10～15min after, continue add 90～
The copper sulphate pentahydrate of 100mg and the deionized water of 600～610mL, at 20～30 DEG C stirring mixing 10～
15min；To be mixed complete after, its intensification is heated to 250～280 DEG C so that it is reaction 4～5h, treat that it is anti-
After should completing so that it is stand and be cooled to 20～30 DEG C, collect yellow reaction liquid and to its sucking filtration, collect filtrate
And it is slowly added dropwise the sulfuric acid solution that mass concentration is 10%, treat that white precipitate slowly separates out, measure its pH
When being 3～4, stop dropping sulphuric acid and be allowed to rest for precipitating 20～30min；After standing completes, it is taken out
Filter and collect filter cake, being 7.0 to its drip washing to filtrate pH with deionized water, be subsequently placed at 60～80 DEG C
Baking oven is dried 6～8h, is prepared into 4,4 ' dihydroxybiphenyls, is placed in 50～60 DEG C of baking ovens, dry
Dry preservation；In the there-necked flask of 100mL, the dimethylformamide 4.5～5.0g of addition 50～55mL
The 4 of above-mentioned preparation, 4 ' dihydroxybiphenyls and 2.7～the o-methoxybenzaldehyde of 3.0g, at 60～65 DEG C
It is made to stir mixing 10～15min；To be mixed complete after, continue add 4.5～5.0g mass concentration be 30%
Sodium methoxide solution, after there is greenish yellow solid in it, insulation reaction 30～40min, subsequently stop heating also
Place reaction liquid in frozen water, it stirred and filters, collect filtering residue and be placed at 60～80 DEG C being dried 6～8h,
Double (2-methoxybenzoic acid base) biphenyl of 4,4-can be prepared into.
Example 1
By the 4 of 17g, 4-'-dibromobiphenyl and the sodium hydroxide solution stirring mixing that 32mL mass concentration is 15%, juxtaposition
In the autoclave of 1L, after its stirring mixing 10min, continue to add copper sulphate pentahydrate and the 600mL of 90mg
Deionized water, at 20 DEG C stirring mixing 10min；To be mixed complete after, its intensification is heated to 250 DEG C,
Make it react 4h, after it has reacted so that it is to stand and be cooled to 20 DEG C, collect yellow reaction liquid and to it
Sucking filtration, collects filtrate and it is slowly added dropwise the sulfuric acid solution that mass concentration is 10%, treating that white precipitate is slowly analysed
Go out, measure its pH when being 3～4, stop dropping sulphuric acid and be also allowed to rest for precipitating 20min；After standing completes,
To its sucking filtration and collect filter cake, it is 7.0 to its drip washing to filtrate pH with deionized water, is subsequently placed at 60 DEG C
Baking oven is dried 6h, is prepared into 4,4 ' dihydroxybiphenyls, is placed in 50 DEG C of baking ovens, kept dry；
In the there-necked flask of 100mL, 4, the 4 ' of the above-mentioned preparation of the dimethylformamide 4.5g of addition 50mL
Dihydroxybiphenyl and the o-methoxybenzaldehyde of 2.7g, make it stir mixing 10min at 60 DEG C；To be mixed
After completing, continue to add the sodium methoxide solution that mass concentration is 30% of 4.5g, treat that it greenish yellow solid occurs
After, insulation reaction 30min, stop heating subsequently and place reaction liquid in frozen water, it stirred and filters,
Collect filtering residue to be placed at 60 DEG C being dried 6h, 4 can be prepared into, double (2-methoxybenzoic acid base) biphenyl of 4-.
Example 2
By the 4 of 17.5g, 4-'-dibromobiphenyl and the sodium hydroxide solution stirring mixing that 33mL mass concentration is 15%, and
Be placed in the autoclave of 1L, until its stirring mixing 12min after, continue add 95mg copper sulphate pentahydrate and
The deionized water of 605mL, stirring mixing 12min at 25 DEG C；To be mixed complete after, its intensification is heated to
260 DEG C so that it is reaction 4.5h, after it has reacted so that it is stand and be cooled to 24 DEG C, collect yellow reaction
Liquid to its sucking filtration, collects filtrate and also it is slowly added dropwise the sulfuric acid solution that mass concentration is 10%, treat that white is heavy
Form sediment and slowly separate out, measure its pH when being 3, stop dropping sulphuric acid and be also allowed to rest for precipitating 25min；Wait to stand
After completing, to its sucking filtration and collect filter cake, it is 7.0 with deionized water to its drip washing to filtrate pH, subsequently will
It is placed in 60 DEG C of baking ovens and is dried 7h, is prepared into 4,4 ' dihydroxybiphenyls, is placed in 55 DEG C of baking ovens,
Kept dry；In the there-necked flask of 100mL, add the above-mentioned preparation of the dimethylformamide 4.7g of 52mL
4,4 ' dihydroxybiphenyls and the o-methoxybenzaldehyde of 2.8g, make at 62 DEG C its stir mixing 12min；
To be mixed complete after, continue add 4.5～5.0g the sodium methoxide solution that mass concentration is 30%, treat that it occurs
After greenish yellow solid, insulation reaction 35min, stop heating subsequently and place reaction liquid in frozen water, it is stirred
Mix and filter, collect filtering residue and be placed at 70 DEG C being dried 7h, 4 can be prepared into, the double (2-methoxybenzoic acid of 4-
Base) biphenyl.
Example 3
By the 4 of 18g, 4-'-dibromobiphenyl and the sodium hydroxide solution stirring mixing that 35mL mass concentration is 15%, juxtaposition
In the autoclave of 1L, after its stirring mixing 15min, continue to add copper sulphate pentahydrate and the 610mL of 100mg
Deionized water, at 30 DEG C stirring mixing 15min；To be mixed complete after, its intensification is heated to 280 DEG C,
Make it react 5h, after it has reacted so that it is to stand and be cooled to 30 DEG C, collect yellow reaction liquid and to it
Sucking filtration, collects filtrate and it is slowly added dropwise the sulfuric acid solution that mass concentration is 10%, treating that white precipitate is slowly analysed
Go out, measure its pH when being 4, stop dropping sulphuric acid and be also allowed to rest for precipitating 30min；After standing completes,
To its sucking filtration and collect filter cake, it is 7.0 to its drip washing to filtrate pH with deionized water, is subsequently placed at 80 DEG C
Baking oven is dried 8h, is prepared into 4,4 ' dihydroxybiphenyls, is placed in 60 DEG C of baking ovens, kept dry；
In the there-necked flask of 100mL, 4, the 4 ' of the above-mentioned preparation of the dimethylformamide 5.0g of addition 55mL
Dihydroxybiphenyl and the o-methoxybenzaldehyde of 3.0g, make it stir mixing 15min at 65 DEG C；To be mixed
After completing, continue to add the sodium methoxide solution that mass concentration is 30% of 5.0g, treat that it greenish yellow solid occurs
After, insulation reaction 40min, stop heating subsequently and place reaction liquid in frozen water, it stirred and filters,
Collect filtering residue to be placed at 80 DEG C being dried 8h, 4 can be prepared into, double (2-methoxybenzoic acid base) biphenyl of 4-.
Claims (1)
1. one kind 4, the synthetic method of double (2-methoxybenzoic acid base) biphenyl of 4-, it is characterised in that concrete synthesis step is:
(1) 4,4-'-dibromobiphenyl and 32～35mL mass concentrations by 17～18g are the sodium hydroxide solution of 15%
Stirring mixing, be placed in the autoclave of 1L, until its stirring mixing 10～15min after, continue add 90～
The copper sulphate pentahydrate of 100mg and the deionized water of 600～610mL, at 20～30 DEG C stirring mixing 10～
15min；
(2) to be mixed complete after, its intensification is heated to 250～280 DEG C so that it is reaction 4～5h, treat that it reacts
After completing so that it is stand and be cooled to 20～30 DEG C, collect yellow reaction liquid and to its sucking filtration, collect filtrate also
It being slowly added dropwise the sulfuric acid solution that mass concentration is 10%, treats that white precipitate slowly separates out, measuring its pH is
When 3～4, stop dropping sulphuric acid and be allowed to rest for precipitating 20～30min；
(3) after standing completes, to its sucking filtration and collect filter cake, with deionized water to its drip washing to filtrate pH it is
7.0, it is subsequently placed in 60～80 DEG C of baking ovens and is dried 6～8h, be prepared into 4,4 ' dihydroxybiphenyls, will
It is placed in 50～60 DEG C of baking ovens, kept dry；
(4) in the there-necked flask of 100mL, dimethylformamide 4.5～5.0g above-mentioned of 50～55mL is added
4,4 ' dihydroxybiphenyls of preparation and the o-methoxybenzaldehyde of 2.7～3.0g, make it at 60～65 DEG C
Stirring mixing 10～15min；
(5) to be mixed complete after, continue add 4.5～5.0g the sodium methoxide solution that mass concentration is 30%, treat
After there is greenish yellow solid in it, insulation reaction 30～40min, stop heating subsequently and place reaction liquid into frozen water
In, it stirred and filters, collecting filtering residue and be placed at 60～80 DEG C being dried 6～8h, 4,4-can be prepared into
Double (2-methoxybenzoic acid base) biphenyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610200241.XA CN105801420A (en) | 2016-03-31 | 2016-03-31 | Synthetic method of 4,4-bis(2-methoxy benzoyloxy)biphenyl |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610200241.XA CN105801420A (en) | 2016-03-31 | 2016-03-31 | Synthetic method of 4,4-bis(2-methoxy benzoyloxy)biphenyl |
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| Publication Number | Publication Date |
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| CN105801420A true CN105801420A (en) | 2016-07-27 |
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| CN201610200241.XA Pending CN105801420A (en) | 2016-03-31 | 2016-03-31 | Synthetic method of 4,4-bis(2-methoxy benzoyloxy)biphenyl |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104119223A (en) * | 2014-08-01 | 2014-10-29 | 山东华氟化工有限责任公司 | Preparation method of difluoroacetic acid alkyl ester |
| CN104628559A (en) * | 2013-11-06 | 2015-05-20 | 连云港金康医药科技有限公司 | Ozone oxidation method used for preparing halogenated acetic acid and esters of halogenated acetic acid |
-
2016
- 2016-03-31 CN CN201610200241.XA patent/CN105801420A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104628559A (en) * | 2013-11-06 | 2015-05-20 | 连云港金康医药科技有限公司 | Ozone oxidation method used for preparing halogenated acetic acid and esters of halogenated acetic acid |
| CN104119223A (en) * | 2014-08-01 | 2014-10-29 | 山东华氟化工有限责任公司 | Preparation method of difluoroacetic acid alkyl ester |
Non-Patent Citations (1)
| Title |
|---|
| 陈冰等: "负载型钾盐催化剂用于合成苯甲醚的研究者", 《燃料化学学报》 * |
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Application publication date: 20160727 |
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