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1,1-diacetate synthesis catalyzed by sulfonated cage-type mesoporous carbon

A technology of sulfonated cage type and diacetate, which is applied in the field of carbonyl ester compounds, can solve the problems of low recycling rate, long reaction time, and difficult separation of products, and achieve short reaction time, mild reaction conditions, and high yield. high rate effect

Inactive Publication Date: 2013-09-25
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the main disadvantages of the above catalysts are strong acid conditions, long reaction time, low yield and selectivity, difficult product separation, high price, low recycling rate, etc.

Method used

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  • 1,1-diacetate synthesis catalyzed by sulfonated cage-type mesoporous carbon
  • 1,1-diacetate synthesis catalyzed by sulfonated cage-type mesoporous carbon
  • 1,1-diacetate synthesis catalyzed by sulfonated cage-type mesoporous carbon

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Taking the synthesis of 1,1-diacetoxy-1-(2-trifluoromethylphenyl)methane as an example, 1,1-diacetoxy-1-(2-trifluoromethylphenyl)methane The structural formula is:

[0024]

[0025] Its synthetic method is as follows:

[0026] Add 2mmol of 2-trifluoromethylbenzaldehyde, 5mmol of acetic anhydride, and 30mg of sulfonated cage-type mesoporous carbon into a 25mL single-necked bottle, stir and react for 5 minutes at room temperature without solvent, track the reaction until complete by TLC, add ethyl acetate 20-30mL, filter the catalyst, and use saturated NaHCO 3 The solution was washed 3 times, washed 1 time with water, and the organic phase was washed with anhydrous Na 2 SO 4 After drying, the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was separated by column chromatography (the volume ratio of ethyl acetate to petroleum ether was 1:8 as the eluent) to obtain the pure product with a yield of 96%, m.p.71-72°C; 1 H NMR ...

Embodiment 2

[0029] Taking the synthesis of 1,1-diacetoxy-1-(2-bromo-4,5-dimethoxyphenyl)methane as an example, 1,1-diacetoxy-1-(2-bromo-4 ,5-dimethoxyphenyl)methane has the structural formula:

[0030]

[0031] Its synthetic method is as follows:

[0032] Add 2mmol of 2-bromo-4,5-dimethoxybenzaldehyde, 5mmol of acetic anhydride, and 30mg of sulfonated cage-type mesoporous carbon into a 25mL single-necked bottle, stir and react at room temperature for 5 minutes without solvent, and track the reaction to complete, add 20-30 mL of ethyl acetate, filter the catalyst, and use saturated NaHCO 3 The solution was washed 3 times, washed 1 time with water, and the organic phase was washed with anhydrous Na 2 SO 4 After drying, the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was separated by column chromatography (the volume ratio of ethyl acetate and petroleum ether as the eluent was 1:5) to obtain the pure product with a yield of 97%, m.p.84-85...

Embodiment 3

[0034] Taking the synthesis of 1,1-diacetoxy-1-(phenyl)methane as an example, the structural formula of 1,1-diacetoxy-1-(phenyl)methane is:

[0035]

[0036] Its synthetic method is as follows:

[0037] Add 2 mmol of benzaldehyde, 5 mmol of acetic anhydride, and 30 mg of sulfonated cage-type mesoporous carbon into a 25 mL single-necked bottle, stir and react at room temperature for 5 minutes without solvent, and track the reaction until complete with TLC. Add 20-30 mL of ethyl acetate, filter the catalyst, and wash the filtrate with saturated NaHCO 3 The solution was washed 3 times, washed 1 time with water, and the organic phase was washed with anhydrous Na 2 SO 4 After drying, the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was recrystallized with ethanol to obtain the pure product, the yield was: 96%, m.p.65-66°C, MS (EI): 238 (M + ),179,153,135,107,92,77,43.

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Abstract

The invention relates to 1,1-diacetate synthesis catalyzed by sulfonated cage-type mesoporous carbon. The method is characterized in that aldehyde and acetic anhydride are placed in a reactor according to a molar ratio of 1:1-3; a sulfonated cage-type mesoporous carbon catalyst is added, wherein 5-20mg of the sulfonated cage-type mesoporous carbon catalyst is added to each mole of aldehyde; the materials are stirred under room temperature until a reaction is sufficiently carried out; ethyl acetate with a volume 20-30 times that of the reaction liquid is added; the catalyst is removed by filtering; a filtrate is washed three times by using a saturated NaHCO3 water solution, and once by using water; an organic phase is dried by using anhydrous Na2SO4; the solvent is removed by reduced-pressure distillation under a pressure of 0.09MPa, such that a crude product is obtained; and re-crystallization or column chromatographic separation is carried out, such that 1,1-diacetate is obtained. Compared with existing 1,1-diacetate synthesizing method, the method provided by the invention has the advantages of short reaction time, high yield, mild reaction condition, recyclable catalyst, and the like. The method can be used for synthesizing 1,1-diacetate.

Description

technical field [0001] The invention belongs to the technical field of carbonyl ester compounds, in particular to 1,1-diacetate. Background technique [0002] 1,1-diacetate belongs to alkaloid ester compounds, which are important intermediates in organic synthesis; through the nucleophilic substitution reaction of 1,1-diacetate obtained from aromatic aldehydes, high-yield Obtain nitrile compounds; 1,1-diacetate derived from allyl aldehyde can be converted into poly A useful compound; 1,1-diacetate is also a precursor for the synthesis of acetoxydienes and a substitute for carbonyl compounds in asymmetric synthesis; more attention has been paid to 1,1-diacetate in recent years It has become an important product for the selective protection of aldehyde groups in organic synthesis. [0003] 1,1-Diacetate is usually produced from carbonyl compounds and acetic anhydride in the presence of an acidic catalyst. Catalysts that have been used so far in this reaction are protic acid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/63C07C67/293C07C69/16C07D307/46
CPCY02P20/584
Inventor 李宝林郑彦军卢俊金贾玉才王伟
Owner SHAANXI NORMAL UNIV
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