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Synthesis process of methoxy citronellal

A technology of methoxycitronellal and methoxycitronellol, which is applied in the field of synthesis of methoxycitronellal, can solve the problems of low total yield, unfavorable safety environment and the like, achieves mild reaction conditions, The effect of high yield and easy industrial production

Inactive Publication Date: 2005-12-21
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthetic technique has the advantages of mild reaction conditions and easy operation, but the total yield is not high (about 30%), and there are problems such as safety and unfavorable environment (the use of Collins reagent and concentrated sulfuric acid)

Method used

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  • Synthesis process of methoxy citronellal

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Treat the commercially available strongly acidic cation exchange resin with 1M hydrochloric acid solution at a ratio of liquid to solid mass ratio of 10 at room temperature for 20 hours, filter and wash with deionized water until there is no chloride ion (tested by silver nitrate solution), and store at 60°C Dry for 48 hours to obtain a hydrogen-type strongly acidic cation exchange resin, which is set aside.

[0020] Add 156g (1mol) of citronellol, 128g (4mol) of methanol, and 30g of hydrogen-form strongly acidic cation exchange resin into a 500mL three-necked flask in sequence, and heat the mixture to 60°C under stirring for 15h, cool naturally, and filter. Filtrate with saturated NaHCO 3 Solution washing to neutral, distilled water washing, saturated brine washing, anhydrous MgSO 4 dry. Evaporate the solvent, rectify under reduced pressure, and collect fractions at 128-130°C / 350Pa to obtain 162.6 g of methoxycitronellol as a colorless liquid, with a yield of 86.5%. ...

Embodiment 2

[0023] Treat the commercially available strongly acidic cation exchange resin with 2M hydrochloric acid solution at a ratio of liquid to solid mass ratio of 6 for 24 hours at room temperature, filter and wash with deionized water until there is no chloride ion (tested by silver nitrate solution), and store at 80°C Dry for 24 hours to obtain a hydrogen-type strongly acidic cation exchange resin, which is ready for use.

[0024] Add 156g (1mol) of citronellol, 192g (6mol) of methanol, and 40g of hydrogen-form strongly acidic cation exchange resin into a 1000mL three-necked flask in sequence, and heat the mixture to 65°C under stirring for 20h, cool naturally, and filter. Filtrate with saturated NaHCO 3 Solution washing to neutral, distilled water washing, saturated brine washing, anhydrous MgSO 4 dry. The solvent was evaporated, rectified under reduced pressure, and the fraction at 110-112°C / 150Pa was collected to obtain 168.3 g of methoxycitronellol as a colorless liquid, wit...

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Abstract

The present invention relates to the synthesis method of methoxy citronellal, comprising the following steps: 1) preparation of hydrogen type strongly acidic cation exchange resin catalyst: use hydrochloric acid to soak the strongly acidic cation exchange resin for modification treatment; 2) citronellol , methanol and the hydrogen-type strongly acidic cation exchange resin catalyst prepared in step 1), after mixing, heating and reacting under stirring conditions, the reaction temperature is 20-100 ° C, and the reaction time is 0.5-48h to obtain a colorless liquid methoxy citronella alcohol; 3) after mixing chromium trioxide pyridine hydrochloride and dichloromethane at 0-40°C, stir and drop the methoxycitronellol prepared in step 2) to obtain a colorless liquid methoxycitronellol Mouthal. The method for synthesizing methoxycitronellal of the present invention has the characteristics of simple operation, mild reaction conditions, safety, relative environmental protection and high yield, and is easy to carry out industrialized production.

Description

technical field [0001] The invention relates to a synthesis method of methoxycitronellal (7-methoxy-3,7-dimethyloctylaldehyde). Background technique [0002] Methoxycitronellal, whose chemical name is 7-methoxy-3,7-dimethyloctanal, and whose foreign trade name is Melonia, is a spice and fine chemical raw material widely used at home and abroad. It has fresh green, leaf and lily-of-the-valley aromas, and can be used in the formulation of daily chemical essences, and is also one of the important raw materials for the synthesis of methoxy juvenile hormone analogues. [0003] There are many reports on the synthesis of methoxycitronellal. What have is with citronellal as raw material, after forming Schiff base with amines, under sulfuric acid catalysis, carbon-carbon double bond and methanol carry out etherification reaction and deamination to obtain target product (Vrba, Zdenek & Pokomy.Mikic Czech.CS 246, 341,1985); or use hydroxycitronellal as raw material, first form Schiff...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/64C07C47/198
Inventor 江焕峰朱新海许琳赵妍冉学光
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI