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Synthesizing process of cis-dihydro jasmine keto-acid methyl ester

A technology of methyl dihydrojasmonate and methyl jasmonate, which is applied in the field of preparation of fragrance compounds, can solve the problem of low content of cis-methyl dihydrojasmonate, thermodynamic instability of cis structure, reaction There are many steps to achieve the effect of easy industrial production, mild reaction conditions and simple operation

Active Publication Date: 2007-07-18
ZHEJIANG NHU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But whole synthetic route reaction step is many, because cis-structure is unstable in thermodynamics, it isomerization and other problems take place in follow-up steps, make total yield and cis-dihydrojasmonate methyl ester low content

Method used

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  • Synthesizing process of cis-dihydro jasmine keto-acid methyl ester
  • Synthesizing process of cis-dihydro jasmine keto-acid methyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 113.60g (0.50mol) of ordinary methyl dihydrojasmonate, 60.00g (0.55mol) of trimethylchlorosilane, and 1.14g of acetic acid into a 250ml four-necked flask in turn, and heat the mixture to 60°C under stirring. 8hr, during the reaction, monitor the content of trans-methyl dihydrojasmonate, when the content of trans-methyl dihydrojasmonate drops below 1%, add an appropriate amount of sodium carbonate to neutralize, stop reaction. After the reaction, recover excess trimethylchlorosilane, control the temperature not to exceed 60°C, and cool naturally after recovery to obtain compound II for future use.

[0024] Heat the compound II prepared above to 95°C, add 20.00g of sodium acetate first, then start to add 42.00g of bromine dropwise, finish dropping in 120min, keep it warm for 260min, then cool down to room temperature to obtain compound III, set aside.

[0025] In a 500ml four-neck flask, add 200ml200 # Solvent oil and 15.00g sodium carbonate, stir and heat up to 185...

Embodiment 2

[0028] 227.20g (1.0mol) common methyl dihydrojasmonate, 122.20g (1.2mol) isopropenyl acetate, 1.38g p-toluenesulfonic acid and 1.00g acetic acid mixed acid were added successively in a 500ml four-necked flask, and the mixture Heating to 80°C under stirring for 6 hours, during the reaction, monitor the content of trans-methyl dihydrojasmonate, when the content of trans-methyl dihydrojasmonate drops below 1%, add an appropriate amount The reaction stopped after neutralization with potassium oxalate. After the reaction, cool naturally, then reclaim excess isopropenyl acetate under vacuum conditions, control the temperature not to exceed 80°C, cool naturally after recovery, and set aside.

[0029] Cool the compound II prepared above to 0°C, add 30.00g of potassium oxalate first, then start to pass through 1.0mol of chlorine gas for 120min, then keep it warm for 60min and then naturally warm up to room temperature for later use.

[0030] Add 180ml of ethyl acetate and 25.00g of ca...

Embodiment 3

[0033] Add 113.60g (0.5mol) of ordinary methyl dihydrojasmonate, 77.00g (0.55mol) of phosphorus trichloride, and 1.14g of benzenesulfonic acid into a 250ml four-necked flask in sequence, and heat the mixture to 60°C under stirring React for 8 hours, during the reaction, monitor the content of trans-methyl dihydrojasmonate, when the content of trans-methyl dihydrojasmonate drops below 1%, add an appropriate amount of sodium citrate for neutralization , stop responding. After the reaction, recover excess phosphorus trichloride, control the temperature not to exceed 60°C, and cool naturally after recovery to obtain compound II for future use.

[0034] Heat up the compound II prepared above to 55°C, first add 30.00g sodium citrate, then start to add 128.00g iodine, finish adding in 30 minutes, then keep warm for 30 minutes and then cool to room temperature to obtain compound III, which is set aside.

[0035] Add 120ml of xylene and 15.00g of sodium hydroxide in turn to a 500ml fo...

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Abstract

This invention involves a cis-dihydrojasmone acid methyl ester synthetic method. The existing multi-step synthesis method is low yield and product content. This invention takes ordinary dihydrojasmone acid methyl ester as raw material, by enolase reaction and halogenation reaction, to dehalogenate to prepare double bonds jasmonate methyl ester; finally, under the solvent-free state through hydrogenation to obtain cis-dihydrojasmone acid methyl ester.

Description

technical field [0001] The invention relates to the preparation of fragrance compounds, in particular to a synthesis method of cis-methyl dihydrojasmonate. Background technique [0002] Methyl dihydrojasmonate (chemical name: methyl 2-pentyl-3-carbonylcyclopentyl acetate) has the following four structural formulas. Ordinary methyl dihydrojasmonate is mainly trans-structured methyl dihydrojasmonate, which has an elegant and soft jasmine fragrance and a comfortable lemon-like fruity fragrance. The whole fragrance is light and elegant, and the fragrance lasts for a long time. Fragrance effect is good. [0003] [0004] Compared with ordinary methyl dihydrojasmonate, cis-methyl dihydrojasmonate has a super aroma enhancing effect in the fresh modern floral aroma, and its intensity is much higher than that of ordinary dihydrojasmonate Acid methyl ester, with strong and precious floral fragrance, like jasmine, sweet and long-lasting, slightly powdery fragrance, good diffusibil...

Claims

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Application Information

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IPC IPC(8): C07C67/30C07C67/303C07C69/716
Inventor 季根忠鲁国彬谢小波鲁云卢柳春
Owner ZHEJIANG NHU CO LTD
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