Method of preparing piperonal in one kettle way

A technology of jasmonal and glyoxylic acid, which is applied in the field of one-pot preparation of jasmonal, can solve problems affecting quality and difficult separation, and achieve the effects of simple operation, simplified reaction operation, and mild reaction conditions

Inactive Publication Date: 2010-03-03
上海力智生化科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If 3,4-methylenedioxymandelic acid is directly oxidized without separation, the product will contain tens of ppm of 1,2-methylenedioxy-4-nitrobenzene, which is difficult to separate. Impurities, the product is light yellow, affecting its quality (CN 1400972)

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Into a 2000mL reaction flask, under nitrogen gas flow, 98g (0.8mol) of 1,2-methylenedioxybenzene and 100mL of acetic acid were added. Cool to -10-0°C under stirring, add dropwise a mixed solution consisting of 180g 40% (1mol) glyoxylic acid and 179g concentrated sulfuric acid, and control the temperature at 0-5°C. Stirring was continued for 24 hours after the addition was complete.

[0025] After the reaction, add 4.0g TEBA (triethylbenzyl ammonium chloride), 400mL water and 250mL toluene to the reaction system, and add 65g concentrated nitric acid at 0-5°C, react at room temperature for 1 hour and then heat up to 40-50°C , continue to react for half an hour. After the reaction solution was cooled to room temperature, the organic layer was separated, and the aqueous layer was extracted with toluene (50 mL×2). The organic layer was washed successively with aqueous sodium bicarbonate solution and water, dried and recovered toluene. Distilled under reduced pressure to o...

Embodiment 2

[0027] In a 2000mL reaction flask, nitrogen was passed through, and 98g (0.8mol) of 1,2-methylenedioxybenzene and 80mL of acetic acid were added. Cool to -10-0°C under stirring, add dropwise a mixed solution consisting of 180g 40% (1mol) glyoxylic acid and 179g concentrated sulfuric acid, and control the temperature at 0-5°C. Stirring was continued for 24 hours after the addition was complete.

[0028] After the reaction, add 10g of β-cyclodextrin, 400mL of water and 250mL of toluene to the reaction system, and add 65g of concentrated nitric acid at 0-5°C, react at room temperature for 1 hour, then raise the temperature to 40-50°C, and continue the reaction for half an hour. After the reaction solution was cooled to room temperature, the organic layer was separated, and the aqueous layer was extracted with toluene (50 mL×2). The organic layer was washed successively with aqueous sodium bicarbonate solution and water, dried and recovered toluene. Distilled under reduced press...

Embodiment 3

[0030] Nitrogen was passed through the reaction flask, and 98 g (0.8 mol) of 1,2-methylenedioxybenzene and 100 mL of formic acid were added. Cool to -10~0°C under stirring, add dropwise a mixed solution consisting of 200g 40% (1.2mol) glyoxylic acid and 200g phosphoric acid, and control the temperature at 0~5°C. Stirring was continued for 24 hours after the addition was complete. After the reaction is over, add 10g of β-cyclodextrin, 400mL of water and 200mL of benzene into the reaction system, and add 65g of concentrated nitric acid at 0-5°C, react at room temperature for 1 hour, then raise the temperature to 40-50°C, and continue the reaction for half an hour. After the reaction solution was cooled to room temperature, the organic layer was separated, and the aqueous layer was extracted with toluene. The solvent was recovered after the organic layer was washed and dried. Distillation under reduced pressure gave 90 g of the product (yield 75%, content ≥ 99%).

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PUM

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Abstract

The invention relates to a method of preparing piperonal in a one kettle way, which is a technical improvement of using 1,2-(methylenedioxy) benzene as a raw material to synthesize the piperonal. By the measures of selecting a proper solvent, adding an additive, diluting a reaction solution, and the like, the intermediate 3,4-(methylenedioxy) mandelic acid can be directly oxidized without being separated and purified to synthesize the piperonal in the 'one kettle' way. The invention has the characteristics of simple operation, high yield and the like, and both the purity and the quality of theproduct meet the requirements.

Description

technical field [0001] The invention relates to a method for preparing jasmonal in one pot. Background technique [0002] Jasminal is an important spice with sweet heliotrope aroma, light and slightly sweet cherry and sunflower aroma and faint spicy aroma. It is a safe spice approved by the American Spice Extract Manufacturing Association and is used in spices and Condiment industry, as well as the brightening agent of metal plating, and also the synthetic raw material of medicine and pesticide. [0003] The chemical name of jasmonal is 3,4-dioxymethylenebenzaldehyde. The commonly used synthetic method is to use 1,2-methylenedioxybenzene as the raw material, firstly prepare the intermediate 3,4-methylenedioxymandelic acid, and then obtain it by oxidation. After two steps of reaction. [0004] The intermediate 3,4-methylenedioxymandelic acid is generally prepared by reacting 1,2-methylenedioxybenzene and glyoxylic acid under acidic conditions (JP2002114774; JP08059650; CN1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/54
Inventor 朱红刘锡玲
Owner 上海力智生化科技有限公司
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