Method for preparing citral through dehydrolinalool rearrangement reaction

A technology for dehydrolinalool and rearrangement reactions, applied in catalytic reactions, preparation of carbon-based compounds, chemical instruments and methods, etc., to achieve high reactivity and selectivity, convenient source, good economic benefits and application prospects

Active Publication Date: 2021-08-13
江苏宏邦化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when DMSO is heated in the presence of acid, it will produce a small amount of compounds with malodorous odors such as methyl mercaptan and dimethyl sulfide, which cannot be applied in the current industry where green environmental protection is the mainstream.

Method used

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  • Method for preparing citral through dehydrolinalool rearrangement reaction
  • Method for preparing citral through dehydrolinalool rearrangement reaction
  • Method for preparing citral through dehydrolinalool rearrangement reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 0.152g (1mmol) dehydrolinalool, 3.26mg (0.01mmol) MoO 2 (acac) 2 , 55.6mg (0.2mmol) Ph 3 Add PO, 35.6mg (0.2mmol) 4-tert-butylbenzoic acid and 4mL solvent toluene into a thick-walled pressure-resistant reaction bottle, and put it into a 120 o After reacting 7h in C oil bath, monitor reaction by thin-layer chromatography completely, by 1 H-NMR internal standard method was used to measure the yield of the target product, and the yield of the target product citral was measured to be 53%.

Embodiment 2

[0037] With 0.152g (1mmol) dehydrolinalool, 4.89mg (0.015mmol) MoO 2 (acac) 2 , 55.6mg (0.2mmol) Ph 3 Add PO, 35.6mg (0.2mmol) 4-tert-butylbenzoic acid and 4mL solvent toluene into a thick-walled pressure-resistant reaction bottle, and put it into a 120 o After reacting 7h in C oil bath, monitor reaction by thin-layer chromatography completely, by 1 H-NMR internal standard method was used to determine the yield of the target product, and the yield of the target product citral was measured to be 67%.

Embodiment 3

[0039] With 0.152g (1mmol) dehydrolinalool, 9.78mg (0.03mmol) MoO 2 (acac) 2 , 55.6mg (0.2mmol) Ph 3 Add PO, 35.6mg (0.2mmol) 4-tert-butylbenzoic acid and 4mL solvent toluene into a thick-walled pressure-resistant reaction bottle, and put it into a 120 o After reacting 7h in C oil bath, monitor reaction by thin-layer chromatography completely, by 1 H-NMR internal standard method was used to determine the yield of the target product, and the yield of the target product citral was 70%.

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Abstract

The invention discloses a method for synthesizing citral by rearranging dehydrolinalool serving as a raw material. The method comprises the following steps: adding a catalytic system MoO2(acac)2 and Ph3PO into dehydrolinalool serving as the raw material in the presence of a solvent methylbenzene and an organic acid 4-tert-butylbenzoic acid, and catalyzing Meyer-Schuster rearrangement reaction to obtain citral. The catalyst system used in the invention can obtain citral with relatively high activity and selectivity and relatively ideal conversion rate and yield, the reaction process is green and environment-friendly, and harmful and odorous mercaptan and thioether are not generated. The catalytic system provides an improved method for the preparation of citral, avoids the use of sulfoxide compounds, and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of citral, in particular to a method for preparing citral through dehydrolinalool rearrangement reaction. Background technique [0002] Citral, chemical name 3,7-dimethyl-2,6-octadienal, has two cis-trans isomers, namely geranial (E-citral) and neral (Z -citral) is a light yellow transparent liquid with a strong lemon aroma, which can be used in cosmetics and food flavors. Citral is also a raw material for the synthesis of ionone series products, which are key intermediates for the synthesis of vitamin A and carotenoid series. [0003] [0004] Citral [0005] Domestic citral products are mainly extracted from plant essential oils, which cannot be produced continuously on a large scale due to the limitation of raw materials. Citral can also be synthesized by some chemical methods. It has been reported that prenaldehyde and 3-methyl-2-buten-1-ol ...

Claims

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Application Information

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IPC IPC(8): C07C45/51C07C47/21B01J31/22
CPCC07C45/512B01J31/2234B01J31/0267B01J2231/52B01J2531/64B01J35/19C07C47/21
Inventor 刘晓涛周振吴庆典杨鹏朱延法
Owner 江苏宏邦化工科技有限公司
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