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Process for preparing cinnamate and derivates thereof

A technology of cinnamate and derivatives, which is applied in the field of preparation of cinnamate and derivatives thereof, can solve the problems of high preparation cost and difficult availability of acetate, and achieve the effects of low organic pollutants and environmental friendliness

Inactive Publication Date: 2008-12-17
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw material α-position halogenated acetate is not easy to obtain, and the preparation cost is relatively high

Method used

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  • Process for preparing cinnamate and derivates thereof
  • Process for preparing cinnamate and derivates thereof
  • Process for preparing cinnamate and derivates thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: preparation of

[0035] Dissolve 10.6g of benzaldehyde (0.1mol) in 50mL of acetone (acetone is in excess), then add 100mL of water, stir at 40°C, add dropwise 10mL of 5% NaOH solution, stir for 1.5 hours to stop the reaction, and use ethyl acetate Extract, dry with anhydrous sodium sulfate, and distill off the solvent under reduced pressure to obtain benzylidene acetone with a yield of 90.0%.

[0036] 6.4 g of copper oxide (0.08 mmol), 20.4 g of iodine (0.08 mmol), 13 mL of pyridine (0.16 mmol) and 100 mL of methanol (large excess of methanol) were added to 5.8 g of benzylidene acetone (0.04 mol) prepared above, Heated under reflux for 32 hours and then cooled, then added 11.0 g of potassium carbonate (0.08 mmol), and continued to reflux and stir for 12 hours to stop the reaction. After cooling, the insoluble matter was removed by filtration, and the filtrate was distilled to obtain the target product with a yield of 58.4%.

[0037] 1 H NMR (CDCl 3 , 60...

Embodiment 2

[0038] Example 2: preparation of

[0039] 6.4 g of copper oxide (0.08 mmol), 20.4 g of iodine (0.08 mmol), 13 mL of pyridine (0.16 mmol) and 100 mL of ethanol (large excess of ethanol) were added to 5.8 g of benzylidene acetone (0.04 mol) prepared above, Heated at reflux for 24 hours and then cooled, then added 11.0 g of potassium carbonate (0.08 mmol), and continued stirring at reflux for 12 hours to stop the reaction. After cooling, the insoluble matter was removed by filtration, and the filtrate was distilled to obtain the target product with a yield of 60.2%.

[0040] 1 H NMR (CDCl 3 , 600MHz), δ(ppm) 7.69(d, J=16.4Hz, 1H), 7.53-7.52(m, 2H), 7.39-7.37(m, 3H), 6.44(d, J=16.4Hz, 1H), 4.27(q, 2H), 1.34(t, 3H).

Embodiment 3

[0041] Example 3: preparation of

[0042] Add 6.4 g of copper oxide (0.08 mmol), 20.4 g of iodine (0.08 mmol), 13 mL of pyridine (0.16 mmol) and 100 mL of isopropanol (isopropyl Large excess of alcohol), reflux heating for 48 hours and then cooling, then added 11.0g of potassium carbonate (0.08mmol), continued reflux and stirring for 12 hours to stop the reaction. After cooling, the insoluble matter was removed by filtration, and the filtrate was distilled to obtain the target product with a yield of 62.8%.

[0043] 1 H NMR (CDCl 3 , 600MHz), δ(ppm) 7.67(d, J=16.4Hz, 1H), 7.53-7.51(m, 2H), 7.39-7.37(m, 3H), 6.42(d, J=16.4Hz, 1H), 5.14 (m, 1H), 1.30 (d, 6H).

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Abstract

The invention relates to a preparation method of cinnamate esters and derivatives thereof, which is shown as the following chart, wherein, R1 is hydrogen, 4-methoxyl or 3-nitryl; R is methyl, ethyl or isopropyl; the preparation takes substituted benzaldehyde and acetone as raw materials and then carries out condensation to obtain substituted benzalacetone under the condition of a NaOH solution. The obtained substituted benzaldehyde carries out 'one-pot' reaction with copper oxide, iodine, pyridine and alcohol, and potassium carbonate is added, and then the cinnamate esters and the derivatives thereof can be obtained. The preparation method of the invention has advantages of cheap raw materials, simple operation, moderate reaction condition and environmental friendliness, and provides a feasible preparation method of the cinnamate esters and the derivatives thereof for industry.

Description

technical field [0001] The invention relates to a preparation method of cinnamate and derivatives thereof. Background technique [0002] Cinnamate is often used in the ingredients of food flavors and daily chemical flavors because of its special fruity or floral fragrance. For example, methyl cinnamate is used as a fixative in spices, often used in the deployment of carnations and oriental floral essences, used in soaps, detergents, flavors and cakes, as an organic synthesis intermediate, mainly used in medicine and pesticides Industry; Ethyl p-methoxycinnamate is the main antifungal active ingredient in the rhizome of Zedoary Curcuma, it has a broad-spectrum antifungal effect, and the minimum inhibitory concentration to Trichophyton rubrum (one of the main pathogens of dermatophytosis) is less than 10mg / L, also has a certain inhibitory effect on other skin pathogenic fungi; octyl p-methoxycinnamate has good absorption ability and high absorption rate for 280nm-320nm ultra...

Claims

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Application Information

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IPC IPC(8): C07C67/42C07C69/618C07C69/736C07C205/56
Inventor 钦静殷国栋王紫华吴彦东佘能芳吴安心
Owner HUAZHONG NORMAL UNIV
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