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Method for synthesizing black nightshade aldehyde

A synthetic method and the technology of solanum aldehyde, which are applied in the field of synthesis of solanum aldehyde, can solve the problems of high cost and unfavorable industrial production, and achieve the effects of low cost, simple reduction method and high yield

Active Publication Date: 2010-12-22
陕西高安绿能生物化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Rivero et al. (Rivero I.A.Org.Prep.Proced.Int., 1993,24,363) proposed the 2-methylphenylethanol oxidation method, although the productive rate is higher, but the reaction temperature will be at-78 ℃, which is unfavorable for suitability for industrialized production
Chen Wanzhi etc. (Chen Wanzhi, Chemical Journal of Universities, 1993,14,1265) utilize various rhodium chelates as catalyst to prepare solanum aldehyde by styrene hydroformylation, which is a relatively new synthetic method, but the cost is higher

Method used

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  • Method for synthesizing black nightshade aldehyde
  • Method for synthesizing black nightshade aldehyde
  • Method for synthesizing black nightshade aldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 2-(α-phenylethyl)benzimidazole methyl iodide salt was synthesized with reference to literature [Craig, J.C.; Erwuibe, N.N.Synthesis, 1981, 4, 303.]. 2-(α-phenylethyl)benzimidazole (synthesized from o-phenylenediamine and α-phenylpropionic acid, reference literature: Shi Zhen, Gu Huan. Chinese Science (B Series), 1996, 26 (5), 403.) under the action of sodium alkoxide, react with methyl iodide at reflux temperature for 18h, ethanol recrystallization promptly obtains 2-(alpha-phenylethyl) benzimidazole methyl iodide salt, productive rate 85%, Elemental analysis, calculated value (%): C53.97, H5.03, N 7.41; found value (%): C 53.94, H 5.09, N 7.38; MS m / z: 251 (M + -I).

[0018] Under stirring, add 0.01mol 2-(α-phenylethyl)benzimidazole methyl iodide salt into 20mL ethanol solution, after adding and dissolving, lower the temperature to 0-5°C, at this temperature, Add 0.02mol sodium chips in batches, keep the temperature and stir for 0.5h, then slowly raise the temperatur...

Embodiment 2

[0020] 2-(α-phenylethyl)benzoxazole ethyl bromide was synthesized with reference to Example 1.

[0021] Under stirring, add 0.01mol 2-(α-phenylethyl)benzoxazolyl ethyl bromide into 30mL ethanol solution, after adding and dissolving, lower the temperature to 0-5°C, at this temperature , add 0.02mol sodium chips in batches, keep the temperature and stir the reaction for 0.5h, slowly raise the temperature to room temperature and then stir the reaction for 0.5h, add 0.01mol sodium chips, and then reflux for 1.5 hours, add 5% hydrochloric acid aqueous solution, make the reaction The mixture was kept at a pH of 3-5 and a temperature of 50-60° C., stirred for 1.5 h, extracted with chloroform (5×30 mL), and evaporated to obtain solanaldehyde. The product is a colorless liquid with a yield of 68%. The NMR, mass spectrometry, infrared and elemental analysis data are consistent with those reported in the literature.

Embodiment 3

[0023] 2-(α-phenylethyl)benzimidazole benzyl chloride was synthesized with reference to Example 1.

[0024] Under stirring, add 0.01mol 2-(α-phenylethyl)benzimidazole benzyl chloride salt into 30mL ethanol solution, after adding and dissolving, lower the temperature to 0-5°C, at this temperature, Add 0.02mol sodium chips in batches, keep the temperature and stir for 0.5h, then slowly raise the temperature to room temperature and then stir for 0.5h, add 0.01mol sodium chips, and then reflux for 1.5 hours, add 5% aqueous hydrochloric acid to make the reaction mixture Keeping the pH value at 3-5 and the temperature at 50-60° C., stir the reaction for 1.5 h, extract with chloroform (5×30 mL), and distill off the solvent to obtain solanin. The product is a colorless liquid with a yield of 62%. The NMR, mass spectrometry, infrared and elemental analysis data are consistent with those reported in the literature.

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Abstract

The present invention discloses one simple process of synthesizing hydratropic aldehyde. The material 2-(alpha-phenyl ethyl) benzimidazole salt, 2-(alpha-phenyl ethyl) benzoxazine salt, 2-(alpha-phenyl ethyl) benzthiazole salt, 2-(alpha-phenyl ethyl) imidazoline salt, 2-(alpha-phenyl ethyl) oxazoline salt, or 2-(alpha-phenyl ethyl) thiazoline salt is produced into hydratropic aldehyde through sodium-alcohol reduction, acid hydrolysis and extraction.

Description

technical field [0001] The invention relates to a synthetic method of solanum aldehyde, which belongs to the technical field of organic chemistry. Background technique [0002] Solanal (2-phenylpropanal) is a precious spice and an important chemical raw material, widely used in spices, medicine, dyes and pesticides and other industries. The industrial production method of Solanum aldehyde is to use acetophenone and ethyl monochloroacetate as raw materials, and synthesize it according to the Darzens method. Acetophenone and ethyl monochloroacetate are prepared under the action of a strong base to produce methyl phenyl glycidic acid ester. The ester is saponified, neutralized, and hydrolyzed into an acid, and then the acid is heated and decomposed to obtain solanaldehyde. This method operation is more complicated, and productive rate and product purity are not high. In order to seek cheaper artificial synthesis routes, many people are engaged in research in this area. River...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/228C07C45/56
Inventor 郭媛李剑利史真
Owner 陕西高安绿能生物化工有限公司
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