Synthetic method of piperonal

A technology of jasmonaldehyde and synthesis method, applied in directions such as organic chemistry, can solve problems such as poor safety, many reaction steps, long routes, etc., and achieve the effects of high safety, few reaction steps, and high yield

Inactive Publication Date: 2014-07-23
李东风
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] The reaction yield of each part of the method is high, but there are many reaction steps and the route is long; the hydrogenation process is used, and the safety is poor

Method used

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  • Synthetic method of piperonal
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  • Synthetic method of piperonal

Examples

Experimental program
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preparation example Construction

[0051] A kind of synthetic method of jasmonal, such as figure 1 shown, including the following steps:

[0052]Step 1. Mix piperonyl cyclocycline, formaldehyde with a concentration of 40% and the preliminary catalyst trimethyldodecyl ammonium bromide with the solvent, then add hydrochloric acid with a concentration of 35%-37%, and statically Place the layers to obtain a piperonyl chloride solution; wherein, the solvent is any one of chloroform, carbon tetrachloride or toluene.

[0053] Prepare ingredients:

[0054] Measure piperonine, hydrochloric acid with a concentration of 35%-37%, and formaldehyde with a concentration of 40%, respectively, and the molar ratio of the three is 1:(1.2-1.5):(1.2-2.0);

[0055] In order to improve the utilization rate of raw materials, preferably, the molar ratio of piperonine, hydrochloric acid and formaldehyde is 1:(1.3-1.4):(1.4-1.6).

[0056] Measure the preliminary catalyst trimethyl dodecyl ammonium bromide, the amount of the preliminar...

Embodiment 1

[0085] In a 500mL flask, add 200ml of solvent chloroform, 61 grams (0.5mol) of piperonylcycline, 46.3 grams (0.63mol) of formaldehyde solution with a concentration of 40%, and 0.5 grams of catalyst trimethyldodecyl ammonium bromide, and stir evenly Finally, 60 grams (0.7 mol) of hydrochloric acid with a concentration of 36% was added dropwise, and the dropwise addition time was controlled at 150 minutes, and reacted at 60° C. for 12 hours, left still, and separated the lower layer oil to obtain a piperonyl chloride trichloromethane solution;

[0086] In the above piperonyl chlorotrichloromethane solution, slowly add unsaturated sodium carbonate solution while stirring, including 31.8 grams (0.3mol) of sodium carbonate, 200mL of water, stir and react at 60°C for 8 hours, and separate the lower organic phase It is jasmonol solution;

[0087] Add 200mL of water to the obtained jasminol solution, fully stir, and wash; two washes can be performed; stand and separate layers to obtai...

example 2

[0092] In 500mL flask, add solvent carbon tetrachloride 200ml, piperonyl cyclocyclone 61 grams (0.5mol), concentration be 46.3 grams (0.63mol) of formaldehyde solution of 40%, catalyzer trimethyl dodecyl ammonium bromide 0.5 grams, stir After being uniform, add 60 grams (0.7 mol) of hydrochloric acid with a concentration of 36% dropwise, and the dropwise addition time is controlled at 150 minutes, and react for 12 hours at 60° C., stand still, and separate the lower layer oil to obtain piperonyl chloride carbon tetrachloride solution;

[0093] In the above-mentioned piperonyl chloride carbon tetrachloride solution, slowly add unsaturated sodium bicarbonate solution while stirring, wherein 52 grams (0.6 mol) of sodium bicarbonate, 200 mL of water, stir and react at 60 ° C for 8 hours, separate The lower organic phase is a jasmonol solution;

[0094] Add 200mL of water to the obtained jasminol solution, fully stir, and wash; two washes can be performed; stand and separate layer...

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Abstract

The invention relates to the technical field of the medical intermediate fine chemical industry and in particular relates to a synthetic method of piperonal. The synthetic method comprises the following steps: 1 uniformly mixing benzodioxole, formaldehyde with concentration of 40% and a primary catalyst dodecyl trimethyl ammonium bromide with a solvent, then adding hydrochloric acid with concentration of 35-37% and standing for layering after reaction, thus obtaining a piperonyl chloride solution, wherein the solvent is trichloromethane, tetrachloromethane or methylbenzene; 2 preparing a sodium bicarbonate or sodium carbonate water solution with concentration less than or equal to that of a saturated solution, adding the sodium bicarbonate or sodium carbonate water solution to the piperonyl chloride solution and reacting to obtain a piperonyl alcohol solution; 3 introducing air into the piperonyl alcohol solution to oxidize the piperonyl alcohol solution to generate a piperonal solution by using both ferric nitrate and 4-hydroxy-2,2,4,4-methylpiperidine nitroxyl free radical as final catalysts. The synthetic method provided by the invention has the advantages of accessible raw materials, mild reaction conditions, stable and high yield, few byproducts and low cost.

Description

technical field [0001] The invention relates to the technical field of fine chemical industry of pharmaceutical intermediates, in particular to a method for synthesizing jasmonal. Background technique [0002] Piperonal (piperonal, CAS120-57-0), also known as piperonal, the chemical name is 3,4-dioxymethylene benzaldehyde. Jasminal is a white shiny crystal with the molecular formula C 8 h 6 o 3 , molecular weight 150.14, melting point 35-37°C, boiling point 261-263°C, with sweet heliotrope aroma, faint spicy aroma, weak aroma but long-lasting fragrance. Jasmonal is naturally present in plants such as sassafras oil, vanilla, and violet flowers. [0003] Jasminal is a kind of precious spice with a wide range of uses, and it has been selling well in the international market for decades. The main raw material for producing jasmonal is sassafras oil, which contains 75-85% sassafras oil. In the past, it has always been extracted from the roots of sassafras. [0004] People i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/54
CPCC07D317/54
Inventor 李东风
Owner 李东风
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