Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthesis method of trans-alpha-benzoinoxime

A technology of benzoin oxime and synthesis method, which is applied in the field of organic chemical synthesis, can solve problems such as low selectivity, reduced use efficiency, and difficult separation operation, and achieve the effect of simple product purification, easy implementation, and improved separation efficiency

Active Publication Date: 2012-10-03
TSINGHUA UNIV
View PDF5 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the reaction of α-benzoin oxime to generate α-benzoin oxime, two isomers of cis and trans are often obtained, and the selectivity of the reaction is low
Moreover, the two isomers have similar structures and similar physical properties, which brings certain difficulties to the separation operation.
Commodities in practical applications are often a mixture of two isomers, which greatly reduces the efficiency of use

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis method of trans-alpha-benzoinoxime
  • Synthesis method of trans-alpha-benzoinoxime
  • Synthesis method of trans-alpha-benzoinoxime

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Synthesis of α-benzoin

[0027] 5.3 g (50 mmol) of benzaldehyde, 0.23 g (0.5 mmol) of 1mol% imidazolium salt ionic liquid catalyst and 100 mL of tetrahydrofuran were sequentially added into a 250 mL three-necked flask, heated and stirred to 60 °C, and then 20 mol% sodium hydroxide 0.4 g (10 mmol), the reaction solution was heated to reflux for 8 hours, cooled to room temperature, added 50 mL of water, extracted three times with ethyl acetate, combined the organic phases, washed twice with saturated brine, dried the organic phase with anhydrous sodium sulfate, and filtered , the organic solvent was removed by a rotary evaporator to obtain a light yellow oil; 20 mL of absolute ethanol was added for recrystallization, cooled and filtered to obtain 2.4 g of white needle-shaped crystals, with a yield of 45%.

[0028] 1 H NMR (300 MHz, DMSO-d 6 ): δ 6.02~6.04 (m, 1H, OH), 6.08 (d, 1H, J = 6Hz ), 7.20~7.34 (m, 3H), 7.40~7.48 (m, 4H), 7.54~7.59 (m, 2H ), 7.98~8.01 (m, 2H...

Embodiment 2

[0033] (1) Synthesis of α-benzoin

[0034] 5.3 g (50 mmol) of benzaldehyde, 0.23 g (0.5 mmol) of 1mol% imidazolium salt ionic liquid catalyst and 100 mL of dichloromethane were successively added into a 250 mL three-necked flask, and 0.4 g (10 mmol), the reaction solution was stirred at room temperature for 12 h, added 50 mL of water, extracted three times with ethyl acetate, combined the organic phase, washed twice with saturated brine, dried the organic phase with anhydrous sodium sulfate, filtered, and the organic solvent was removed with a rotary evaporator , to obtain a light yellow oil; recrystallized from a mixed solution of absolute ethanol and petroleum ether to obtain 1.5 g of white needle-like crystals, with a yield of 28%.

[0035] (2) Synthesis of trans-α-benzoin oxime

[0036] Add 1.38 g (6.5 mmol) of α-benzoin, 0.5 g (7.2 mmol) of hydroxylamine hydrochloride and 20 mL of absolute ethanol into a 100 mL single-necked round bottom flask, stir at room temperature f...

Embodiment 3

[0038] (1) Synthesis of α-benzoin

[0039] Add 0.53 g (5 mmol) of benzaldehyde, 23 mg (0.05 mmol) of imidazolium salt ionic liquid catalyst, and 10 mL of tetrahydrofuran into a 50 mL three-necked flask in sequence, heat and stir to 60 °C, then add 40 mg (1 mmol) of sodium hydroxide ), the reaction solution was heated to reflux for 8 hours, cooled to room temperature, added 10 mL of water, extracted three times with ethyl acetate, combined the organic phase, washed twice with saturated brine, dried the organic phase with anhydrous sodium sulfate, filtered, and used for organic solvent Removed by rotary evaporator to obtain an oily substance; recrystallized from a mixed solution of ethyl acetate and petroleum ether to obtain 0.16 g of crystals, with a yield of 30%.

[0040] (2) Synthesis of trans-α-benzoin oxime

[0041] Add 0.15 g (0.7 mmol) of α-benzoin, 54 mg (0.78 mmol) of hydroxylamine hydrochloride and 10 mL of absolute ethanol into a 50 mL single-necked round bottom flas...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a synthesis method of trans-alpha-benzoinoxime and belongs to the field of the organic chemical synthesis technology. The trans-alpha-benzoinoxime is represented by a structural formula (I). The synthesis method comprises catalyzing benzaldehyde through imidazole salt ion liquid, enabling the catalyzed benzaldehyde and benzoin to perform condensation reaction under the alkaline condition to generate alpha-benzoin, enabling alpha-benzoin crude products to be crystallized again, enabling the crystallized alpha-benzoin crude products to react with hydroxylamine hydrochloride or hydroxylamine sulphate to generate the trans-alpha-benzoinoxime, and separating the trans-alpha-benzoinoxime through column chromatography to obtain purified products. The synthesis method of the trans-alpha-benzoinoxime is simple, convenient, mild and environment-friendly in reaction condition, easy to implement, good in yield, low in cost, simple in product purification and capable of obtaining high-purity trans-alpha-benzoinoxime.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a synthesis method of trans-α-benzoin oxime. Background technique [0002] α-Hydroxyxime is an important organic chelating reagent, which is widely used in the fields of mineral processing and metallurgy, mainly for the determination, extraction and separation of metals. For example, the commercial hydroxime extractant LIX63 launched by the General Mining Chemical Company of the United States on the market has a good extraction ability for metal copper, germanium, molybdenum, tungsten, etc., and its composition is 5,8-diethyl-7-hydroxy- Dodecyl-6-ketoxime, but there are cis-trans isomers in this structure, and only the trans-isomer can form complexes with metal ions. It is the active ingredient of the chelated hydroxime extractant LIX63. Trans-α-benzoin oxime is also a kind of α-hydroxy oxime, and it is the active ingredient of testocuproine (coppe...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/48C07C249/08
CPCY02P20/54
Inventor 李晶徐盛明李林艳王俊莲徐刚王学军
Owner TSINGHUA UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com