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The synthetic method of 5-halogenated o-veratraldehyde

A technology of ortho-veratraldehyde and a synthesis method, which is applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of high labor protection cost, limited source of ortho-vanillin, and high price. , to avoid toxic and harmful raw materials, reduce protection costs, and achieve the effect of easy operation

Active Publication Date: 2022-06-24
SICHUAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because it is a by-product of the production of vanillin and ethyl vanillin, the source of o-vanillin is limited, the production capacity is low, and the price is expensive
Secondly, the methylation reactions in the above preparation process all use toxic dimethyl sulfate, so the cost of labor protection is high

Method used

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  • The synthetic method of 5-halogenated o-veratraldehyde
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  • The synthetic method of 5-halogenated o-veratraldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0062] 1.1 Preparation of 4-bromoguaiacol

[0063] Under argon protection, guaiacol (25 g, 201 mmol) was uniformly dispersed in 125 mL of chloroform, and then the reaction solution was pre-cooled at -5 °C for 10 minutes, and bromine (10.3 ml, 201 mmol) was slowly added dropwise thereto. chloroform (75mL) solution, try to keep the system colorless. After the dripping was completed, the reaction was moved to room temperature for 1 hour, and the reaction was detected by TLC dot plate. With 150mL Sat.NaHSO 3 (aq) Quenching the reaction, separating the liquids in a separating funnel, extracting the aqueous layer three times with chloroform, combining the organic phases, backwashing once with saturated brine, drying over anhydrous sodium sulfate and spin-dried to obtain pale yellow crystals Crude. Under reduced pressure distillation (97-100°C / 2mmHg, Lit. 119-120°C / 5mmHg), 4-bromoguaiacol (40g, 94%, mp=31-32°C) was obtained.

[0064] 1 H NMR (400MHz, Chloroform-d) δ 6.99 (dd, J=...

Embodiment 2

[0081] 2.1 Preparation of 4-chloroguaiacol

[0082] Under an ice-salt bath under argon protection (-5°C), guaiacol (12.4 g, 100 mmol) was uniformly dispersed in 50 mL of chloroform, and sulfonyl chloride (13 mL, 160 mmol) was slowly added dropwise thereto. After the dripping was completed, it was moved to 60°C for reflux reaction for 24h, and the reaction was monitored by TLC spot plate. Under ice bath, use 50mL Sat.Na 2 S 2 O 3 The solution was quenched and the reaction was separated in a separating funnel. The aqueous layer was extracted three times with chloroform. The organic phases were combined, backwashed once with saturated brine, dried over anhydrous sodium sulfate and spin-dried to obtain 16.7 g of a brownish-yellow liquid. Crude. After distillation under reduced pressure (82-90°C / 2mmHg, lit.130°C / 7.5mmHg), light yellow oily liquid 4-chloroguaiacol (12.7g, 80%) was obtained with a content of 87% (GC-MS).

[0083] 1 H NMR (400MHz, Chloroform-d) δ6.84(s,3H), 5.61...

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Abstract

The invention belongs to the field of organic chemistry, and specifically relates to a method for synthesizing 5-halogenated o-veratraldehyde, comprising: using 4-halogenated guaiacol as a raw material to prepare 2-hydroxyl-3-methoxyl-5- Halogenated mandelic acid; further use 2-hydroxy-3-methoxy-5-halogenated mandelic acid to obtain 5-halogenated o-vanillin; further use 5-halogenated o-vanillin to obtain 5-halogenated o-Veratraldehyde. The total yield of the synthesis method of the invention is between 60%-70%, and 4-halogenated guaiacol is used as a raw material, which overcomes the problems of limited source of o-vanillin and low production capacity. Simultaneously, in the synthetic method of 5-halogenated o-veratraldehyde of the present invention, other raw materials used are common and easy-to-obtain raw materials, and through the optimization of the reaction procedure, the reaction conditions are mild, the operation is simple, the chemical yield is high, and the cost is low , very suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a method for synthesizing 5-halogenated ortho-veratrol. Background technique [0002] O-veratrol derivatives are an important class of pharmaceutical intermediates, which can be used to synthesize and prepare tetrahydropalmatine derivatives with central sedative effects, berberine derivatives with antibacterial, antiarrhythmic, hypoglycemic effects, etc. Plumbago with expectorant and antitussive effects, codeine analogs with antitussive, sedative and analgesic effects, etc., are widely used. [0003] The ortho-veratraldehyde derivatives are mainly derived from chemical synthesis, and there are not many reports on their preparation processes at home and abroad. Kakde et al. (Org.Lett.2016,18,1752) reported a method for synthesizing 5-bromo-o-veratrol, which was brominated by o-vanillin and then methylated to prepare 5-bromo-o-veratrol Aldehyde, the total yield is 80%...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/64C07C47/575
CPCC07C45/64C07C45/512C07C45/54C07C51/353C07C51/367C07C47/575C07C59/64
Inventor 陈芬儿唐培李伟剑蒋龙
Owner SICHUAN UNIV
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