CN1434030A - 2,5-dimethoxy ethyl phenyl sulfide and synthesis method and use thereof - Google Patents
2,5-dimethoxy ethyl phenyl sulfide and synthesis method and use thereof Download PDFInfo
- Publication number
- CN1434030A CN1434030A CN 03118593 CN03118593A CN1434030A CN 1434030 A CN1434030 A CN 1434030A CN 03118593 CN03118593 CN 03118593 CN 03118593 A CN03118593 A CN 03118593A CN 1434030 A CN1434030 A CN 1434030A
- Authority
- CN
- China
- Prior art keywords
- dimethoxy
- phenyl sulfide
- ethyl phenyl
- sulfonyl chloride
- benzene sulfonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to 2,5-dimethoxyethyl phenyl sulfide and its synthesis method. Said invention provides its structure formula, and uses 2,5-dimethoxybenzenesulfonyl chloride as raw material, and adopts the following steps: using zinc powder to make reduction under the acid condition at 70-80 deg.c, then reduced pressure distilling to obtain 2,5-dimethoxythiophenol, making the obtained 2,5-dimethoxthiophenol implement condensation reaction with bromoethane under the alkaline condition at 70-80 deg.C, reduced pressure distilling to obtain the yellow oil liquor, i.e. the required 2,5-dimethoxyethyl phenyl sulfide. It can be used for synthesizing 2,5-dimethoxy-4-ethylthiobenzaldehyde.
Description
Technical field
The present invention relates to a kind of 2,5-dimethoxy ethyl phenyl sulfide and preparation method and use thereof.
Background technology
As a kind of new compound, 2,5-dimethoxy ethyl phenyl sulfide and synthetic method thereof are not seen bibliographical information as yet.
Summary of the invention
Task of the present invention provides a kind of new compound 2,5-dimethoxy ethyl phenyl sulfide and preparation method and use thereof.
Technical scheme provided by the invention is: 2, and 5-dimethoxy ethyl phenyl sulfide, its structural formula is
The present invention also provides the synthetic method of above-claimed cpd, and with 2,5-dimethoxy benzene sulfonyl chloride is a raw material, under 70～80 ℃, acidic conditions (pH＜1), uses zinc powder reduction, and underpressure distillation then obtains 2,5-dimethoxy thiophenol; It is required 2 that gained 2, the yellow oily liquid that 5-dimethoxy thiophenol obtains with the monobromethane condensation, through underpressure distillation down at 70～80 ℃, alkaline condition (pH＞10) are, 5-dimethoxy ethyl phenyl sulfide.
Above-mentioned 2,5-dimethoxy benzene sulfonyl chloride can prepare by following method: ethylene dichloride and terephthaldehyde's ether are mixed stirring and dissolving, be cooled to 0～10 ℃ of following agitation and dropping chlorsulfonic acid and sulfur oxychloride, tell lower floor's oil reservoir, to its distill yellow solid 2,5-dimethoxy benzene sulfonyl chloride.
The reaction equation of said process is as follows:
2 of the present invention's preparation, 5-dimethoxy ethyl phenyl sulfide can be used for Synthetic 2,5-dimethoxy-4 '-ethyl phenyl sulfide formaldehyde.
Embodiment
In the 250ml there-necked flask, add 105ml ethylene dichloride, 13.5g terephthaldehyde ether, stirring and dissolving, ice bath cooling (0～10 ℃), stir and drip 26.5ml chlorsulfonic acid and 10ml sulfur oxychloride down, reacted 2 hours, and with in its impouring 280ml frozen water, told lower floor's oil reservoir under stirring, steam and remove methylene dichloride (recovery), yellow solid 2,5-dimethoxy benzene sulfonyl chloride, oven-dried weight 19.8g, productive rate 85%, fusing point 115-117 ℃.
In the 500ml there-necked flask, add the 68ml water and the 23ml vitriol oil, when treating that temperature drops to about 70 ℃, adding 12g 2,5-dimethoxy benzene sulfonyl chloride and 18g zinc powder reacted 1 hour down at 80 ℃, and filtration, decompression, steaming are slipped and are obtained 8.2g 2,5-dimethoxy thiophenol.
In the 250ml there-necked flask, add 3g potassium hydroxide and 50ml dehydrated alcohol, stirring and dissolving adds 8g 2, and 5-dimethoxy thiophenol is dissolved in the solution of 20ml dehydrated alcohol, drip the 9g monobromethane again, reflux 1.5h boils off ethanol, uses twice of 40ml dichloromethane extraction, steam except that behind the methylene dichloride, underpressure distillation gets light yellow oily liquid 2,5-dimethoxy ethyl phenyl sulfide 8.2g, productive rate 80%.
2 of the present invention's preparation, 5-dimethoxy ethyl phenyl sulfide can be used for Synthetic 2,5-dimethoxy-4 '-ethyl phenyl sulfide formaldehyde: under the ice bath cooling, the 9.7ml phosphorus oxychloride is joined in the 100ml there-necked flask, drip the 11.5ml dimethyl formamide, drip 8g2 again, 5-dimethoxy ethyl phenyl sulfide, 75 ℃ of stirring reactions 1 hour, placement is spent the night, suction filtration gets light yellow solid (is white solid through the Virahol recrystallization) 8.8g, and this compound is 2,5-dimethoxy-4 '-ethyl phenyl sulfide formaldehyde.
Claims (4)
1. 2,5-dimethoxy ethyl phenyl sulfide, its structural formula is:
2. 2, the synthetic method of 5-dimethoxy ethyl phenyl sulfide is characterized in that: with 2,5-dimethoxy benzene sulfonyl chloride is a raw material, under 70～80 ℃, acidic conditions, uses zinc powder reduction, and underpressure distillation then obtains 2,5-dimethoxy thiophenol; It is required 2 that the yellow oily liquid that gained 2,5-dimethoxy thiophenol obtain with the monobromethane condensation, through underpressure distillation under 70～80 ℃, alkaline condition is, 5-dimethoxy ethyl phenyl sulfide.
3. synthetic method according to claim 2, it is characterized in that: 2,5-dimethoxy benzene sulfonyl chloride makes by following method, ethylene dichloride and terephthaldehyde's ether are mixed stirring and dissolving, be cooled to 0～10 ℃ of following agitation and dropping chlorsulfonic acid and sulfur oxychloride, tell lower floor's oil reservoir, to its distill 2,5-dimethoxy benzene sulfonyl chloride.
4. 2,5-dimethoxy ethyl phenyl sulfide is used for Synthetic 2,5-dimethoxy-4 '-ethyl phenyl sulfide formaldehyde.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03118593 CN1228319C (en) | 2003-02-14 | 2003-02-14 | 2,5-dimethoxy ethyl phenyl sulfide and synthesis method and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03118593 CN1228319C (en) | 2003-02-14 | 2003-02-14 | 2,5-dimethoxy ethyl phenyl sulfide and synthesis method and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1434030A true CN1434030A (en) | 2003-08-06 |
| CN1228319C CN1228319C (en) | 2005-11-23 |
Family
ID=27634448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 03118593 Expired - Fee Related CN1228319C (en) | 2003-02-14 | 2003-02-14 | 2,5-dimethoxy ethyl phenyl sulfide and synthesis method and use thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1228319C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1314666C (en) * | 2005-12-19 | 2007-05-09 | 华中师范大学 | Method for synthesizing thioether compound by aid of microwave |
| CN103787802A (en) * | 2014-02-11 | 2014-05-14 | 华东师范大学 | Aryl alkyl thioether compounds and synthesis method thereof |
-
2003
- 2003-02-14 CN CN 03118593 patent/CN1228319C/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1314666C (en) * | 2005-12-19 | 2007-05-09 | 华中师范大学 | Method for synthesizing thioether compound by aid of microwave |
| CN103787802A (en) * | 2014-02-11 | 2014-05-14 | 华东师范大学 | Aryl alkyl thioether compounds and synthesis method thereof |
| CN103787802B (en) * | 2014-02-11 | 2015-08-19 | 华东师范大学 | One class arylalkyl thioethers compound and synthetic method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1228319C (en) | 2005-11-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101607888B (en) | Alpha-keto-leucine-calcium preparation method | |
| CN101891649A (en) | Novel 3-cyano methyl benzoate preparing method | |
| CN105585454A (en) | Preparation method of hindered bisphenol antioxidant | |
| CN100491346C (en) | Preparation method of 3-mercaptopropionic acid | |
| CN101830866A (en) | Method for preparing bentazone | |
| CN103664923B (en) | The preparation method of Nifuratel | |
| CN1228319C (en) | 2,5-dimethoxy ethyl phenyl sulfide and synthesis method and use thereof | |
| CN1228320C (en) | 2,5-dimethoxy-4-ethyl sulfide-beta-nitrostyrolene and preparation process and use thereof | |
| CN101417956B (en) | Synthesis method of methoxamine hydrochloride | |
| CN1528738A (en) | Method for preparing 2-para octylphenyl ehtyl-2-amino propanediol | |
| CN101125827A (en) | Preparation method of 3-mercaptopropionic acid | |
| CN1260210C (en) | 2,5-dimethoxy-4-ethyl benzaldehyde sulfide and preparation process and use thereof | |
| CN101585778B (en) | Lyrica preparation method | |
| CN1206214C (en) | 2,5-dimethoxy phenylmercaptan and synthesis process and use thereof | |
| CN1228321C (en) | 2-[2'-fluorosulphuric radical] teredimethyl ether and its synthesis and uses | |
| JP4407062B2 (en) | Method for producing diphenyl disulfide derivative | |
| CN102250013B (en) | Preparation method of albendazole | |
| CN1193012C (en) | 2,5-dimethoxy-4-ethyl phenethyl amine sulfide hydrochloride and preparation process and use thereof | |
| CN1228322C (en) | 2,5-dimethoxy-4-[2'-fluorosulphuric radical]-beta-nitro-styrene and its preparation and uses | |
| CN1298687C (en) | Process for preparing 2,3-dichloropropylene | |
| CN1456551A (en) | 2,5-dimethyl-4-[2'-fluorosulphuric radical]-benzaldehyde and its preparation and uses | |
| CN100455557C (en) | Preparation method of methylphenyl acetic acid | |
| CN101343287B (en) | Synthesis of sicycle-ring hexyl di-thiophosphinic acid | |
| CN112225681A (en) | Preparation method of 2, 4-di (n-octylthiomethylene) -6-methylphenol | |
| CN101774983B (en) | Manufacture method of cinepazide maleate compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |