Method for preparing 2,2-dimethyl-3-hydrocinnnamic aldehyde and derivative thereof

A technology of phenylpropanal and derivatives, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of high price of methyl iodide, unfavorable environmental protection, high toxicity and the like

Inactive Publication Date: 2010-03-17
SHANGHAI INST OF TECH
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0002] There is no related synthesis report about compounds 1, 2, and 4. Skouroumounis, G (Helcertica Chimica ACTA, 1996, 79, 1095-1109) et al. used 3-(2,4-dimethylphenyl)-2- Methylpropionaldehyde is a raw material, and compound 3 (HelveticaChimicaActa, 79 (4), 1095-1109, 1996) is obtained after methylation with methyl iodide. There is a raw material in this route that needs to be synthesized, and the price of methyl iodide is also higher, and the toxicity is higher Large, it is also extremely unfavorable to labor protection and environmental protection

Method used

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  • Method for preparing 2,2-dimethyl-3-hydrocinnnamic aldehyde and derivative thereof
  • Method for preparing 2,2-dimethyl-3-hydrocinnnamic aldehyde and derivative thereof
  • Method for preparing 2,2-dimethyl-3-hydrocinnnamic aldehyde and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of 2,2-Dimethyl-3-(2,4-Dimethylphenyl)-1-propanal (Compound 1)

[0031] The first step: the synthesis of 1-(bromomethyl)-2,4-dimethylbenzene

[0032] Add 50 mL of glacial acetic acid, 10.6 g (0.1 mol) of m-xylene, and 3.1 g (0.1 mol) of paraformaldehyde into a 100 mL one-necked flask. After rapid stirring, 16 mL of 40% HBr solution was quickly added to the mixed solution, and the mixture was kept at 80° C. for 8 hours. Then pour it into 100mL of water, separate the liquids, dry the organic phase with anhydrous magnesium sulfate, filter, and decompress the filtrate to obtain 12.3g of 1-(bromomethyl)-2,4-dimethylbenzene with a yield of 62%.

[0033] The second step: the synthesis of 2,2-dimethyl-3-(2,4-dimethylphenyl)-1-propanal

[0034] Under the condition of nitrogen protection, add ground powdery NaOH 2g (50mmol) in the 100mL round bottom flask, phase transfer catalyst tetrabutylammonium bromide (TBAB) 0.5g (10% w / w), toluene 40mL, vigorously stir, The tem...

Embodiment 2

[0037] Synthesis of 2,2-Dimethyl-3-(2,5-Dimethylphenyl)-1-propanal (Compound 2)

[0038] The first step: the synthesis of 1-(bromomethyl)-2,5-dimethylbenzene

[0039] Add 50 mL of glacial acetic acid, 10.6 g (0.1 mol) of p-xylene, and 3.1 g (0.1 mol) of paraformaldehyde into a 100 mL single-necked flask. After rapid stirring, 16 mL of 40% HBr solution was quickly added to the mixed solution, and the mixture was kept at 80° C. for 8 hours. Then it was poured into 100 mL of water, separated, the organic phase was dried with anhydrous magnesium sulfate, filtered, and the filtrate was decompressed to obtain 14.7 g of 1-(bromomethyl)-2,5-dimethylbenzene with a yield of 74%.

[0040] The second step: the synthesis of 2,2-dimethyl-3-(2,5-dimethylphenyl)-1-propanal

[0041] Under the condition of nitrogen protection, 2g (50mmol) of ground powdered NaOH, 0.5g (10% w / w) of phase transfer catalyst tetrabutylammonium bromide (TBAB), 40mL of toluene, and strong Stir and heat up to 70°C....

Embodiment 3

[0044]Synthesis of 2,2-Dimethyl-3-(3,4-Dimethylphenyl)-1-propanal (Compound 3)

[0045] The operation is the same as example 1

[0046] Using o-xylene as the starting substrate, bromination yield: 67% Alkylation yield: 58%, 2,2-dimethyl-3-(2,3-dimethylphenyl)-1- Propionaldehyde: 2,2-dimethyl-3-(3,4-dimethylphenyl)-1-propanal = 4:1. Fragrance description: Translucent floral fragrance, lily of the valley flower fragrance, rabbit ear oxalin.

[0047] 1 HNMR (δ, CDCl 3 ): 1.07(s, 6H, 2C(CH 3 )), 2.50(d, 6H, Ar-CH 3 ), 2.73 (s, 2H, Ar-CH2), 6.83-7.07 (m, 3H, Ar-H), 9.61 (s, 1H, CH=O).IR: KBr, v / cm-13040 (Ar-H stretching vibration), 2965, 2925, 2872 (CH 3 , CH 2 stretching vibration), 1726 (C=O stretching vibration), 1610, 1496, 1470 (CH 3 Asymmetric scissor vibration), 1386 (CH 3 Scissor vibration), 1156; (attached image 3 , attached Figure 7 ).

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Abstract

The invention discloses a method for preparing 2,2-dimethyl-3-hydrocinnnamic aldehyde and a derivative thereof. In the method, the conventional and easily obtained alkyl-substituted benzene (including m-xylene, p-xylene, o-xylene and sym-trimethyl benzene) is taken as the raw material, and the derivative using the 2,2-dimethyl-3-hydrocinnnamic aldehyde as a matrix is obtained through Blanc bromomethylation and isobutylaldehyde alkylation. The method adopts the economical and easily obtained raw materials in the chemical industry market to synthesize the derivatives of the 2,2-dimethyl-3-hydrocinnnamic aldehyde by different methods, and the derivatives are substituted by two methyl in different positions on a benzene ring. The flavors of the derivatives are described. The benzyl bromide and isobutyraldehyde are used for alkylation reaction, thus shortening the reaction time and increasing the yield.

Description

technical field [0001] The invention relates to a preparation method of fragrance raw material 2,2-dimethyl-3-phenylpropanal and derivatives thereof. Background technique [0002] There is no related synthesis report about compounds 1, 2, and 4. Skouroumounis, G (Helcertica Chimica ACTA, 1996, 79, 1095-1109) et al. used 3-(2,4-dimethylphenyl)-2- Methylpropionaldehyde is a raw material, and compound 3 (Helvetica ChimicaActa, 79 (4), 1095-1109, 1996) is obtained after methylation with methyl iodide. There is a raw material in this route that needs to be synthesized, and the price of methyl iodide is also higher simultaneously, and the toxicity is higher Large, it is also extremely unfavorable to labor protection and environmental protection. [0003] [0004] Reaction equation 2.Skouroumounis, the synthetic route of G et al. Contents of the invention [0005] The technical problem to be solved in the present invention is: [0006] 1. Synthesized compounds 1, 2, 4 for t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/228C07C45/68
Inventor 阮礼波潘仙华欧文华刘烽
Owner SHANGHAI INST OF TECH
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