Synthesis method of 4-alkoxyphenol compound

A technology of alkoxyphenol and synthesis method, which is applied in the field of organic chemical synthesis, can solve problems such as limited application and narrow substrate range, and achieve the effects of easy separation and purification, high practicability, and mild reaction conditions

Active Publication Date: 2021-09-28
XINXIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of reaction has many disadvantages, such as the need for harsh conditions such as strict anhydrous and oxygen-free, high temperature and strong alkali, the substrate range is narrow, and it is only suitable for bromo or iodo aromatic hydrocarbons with higher activity, and the substrate needs to be carried out. Halogenated prefunctionalization, however, is also a challenge for highly regioselective halogenation reactions on complex aromatics, which largely limits the application of this type of synthetic method in practical production

Method used

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  • Synthesis method of 4-alkoxyphenol compound
  • Synthesis method of 4-alkoxyphenol compound
  • Synthesis method of 4-alkoxyphenol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]

[0040] Add compound 1a (9mmol), rhodium dipolyacetate (0.135mmol) and iodophendiethyl (9mmol) sequentially into a 75mL pressure tube, then add trifluoroacetic anhydride (30mL), and finally place in an oil bath at 80°C The reaction was carried out under medium magnetic stirring for 1.5 hours. After the reaction was completed, the reaction solution was transferred to a round-bottomed flask, and trifluoroacetic anhydride was distilled off at 70°C, then extracted with ethyl acetate (60mL×3), the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate , the solvent was distilled off under reduced pressure and separated by column chromatography (petroleum ether: ethyl acetate = 8:1, v / v) to obtain the white solid product 2a with a yield of 80%. The compound characterization data are as follows: 1 HNMR (400MHz, Chloroform-d) δ7.44–7.29(m,5H),6.88–6.83(m,2H),6.79–6.73(m,2H),5.01(s,2H),4.53(s,1H) ; 13 C NMR (101MHz, Chloroform-d) δ153.0, 14...

Embodiment 2

[0042]

[0043] Add compound 1b (10mmol), rhodium dipolyacetate (0.15mmol) and iodophendiethyl (10mmol) sequentially into a 75mL pressure tube, then add trifluoroacetic anhydride (30mL), and finally place in an oil bath at 80°C The reaction was carried out under medium magnetic stirring for 1 hour. After the reaction was completed, the reaction solution was transferred to a round-bottomed flask, and trifluoroacetic anhydride was distilled off at 70°C, then extracted with ethyl acetate (60mL×3), the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate , the solvent was distilled off under reduced pressure, and separated by column chromatography (petroleum ether: ethyl acetate = 10:1, v / v) to obtain 2b as a light brown solid with a yield of 95%. The compound characterization data are as follows: 1 HNMR (400MHz, Chloroform-d) δ6.80–6.73(m,4H),4.36(s,1H),3.90(t,J=6.5Hz,2H),1.78–

[0044] 1.69(m, 2H), 1.47(h, J=7.4Hz, 2H), 0.96(t, J=7.4Hz, 3H)...

Embodiment 3

[0047]

[0048] Add compound 1c (0.3mmol), dipolyrhodium acetate (0.45%mmol) and iodobenzenediethyl ester (0.3mmol) successively into a 10mL pressure tube, then add trifluoroacetic anhydride (1.5mL), and finally place Magnetic stirring was carried out in an oil bath at 80°C for 1 hour. After the reaction was completed, 15ml of the reaction was quenched with saturated sodium bicarbonate, then extracted with ethyl acetate (20mL×3), the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and column chromatography separated (Petroleum ether: ethyl acetate = 10:1, v / v) the beige solid product 2c was obtained with a yield of 85%. The compound characterization data are as follows: 1 H NMR (400MHz, Chloroform-d) δ6.81–6.74(m, 4H), 4.71(s, 1H), 3.86(t, J=6.6Hz, 2H), 1.78(h, J=7.1Hz, 2H) ,1.02(t,J=7.4Hz,3H); 13 C NMR (101MHz, Chloroform-d) δ153.2, 149.4, 116.1, 115.7, 70.4, 22.7, 10.5.

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Abstract

The invention discloses a synthesis method of a 4-alkoxyphenol compound, belonging to the field of organic chemical synthesis. The method comprises the following steps: adding an arylalkyl ether compound, a catalyst rhodium acetate dimer and an oxidizing agent diacetoxyiodo ester into a sealed tube, then adding a solvent trifluoroacetic anhydride, and carrying out a heating reaction to prepare the 4-alkoxyphenol compound. According to the invention, the high-regioselectivity direct hydroxylation of the arylalkyl ether compound is achieved, the application range of a substrate is wide, yield is high, activity is not significantly weakened after the amplification reaction, and high yield is still obtained. The synthesis method has good practicability and industrial application prospects.

Description

technical field [0001] The invention relates to a synthesis method of 4-alkoxyphenol compounds, which belongs to the field of organic chemical synthesis. Background technique [0002] 4-Alkoxyphenol compounds are a class of important structural units that widely exist in drug molecules and natural products, and have significant biological activities. In recent years, the synthesis of these compounds has attracted much attention. Since it is one of the challenges in the chemical field to efficiently construct carbon-hydrogen bonds by activating carbon-hydrogen bonds on the benzene ring with high regioselectivity, aryl alkyl ether compounds are used as substrates to achieve selective oxidation of carbon-hydrogen bonds One-step synthesis of 4-alkoxyphenol compounds is undoubtedly of great significance. [0003] Traditional oxidation methods cannot meet the requirements of reactivity and selectivity in this process, and the reaction process is often accompanied by competing si...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/26C07C43/23C07C45/64C07C49/255C07C67/31C07C69/712C07B41/02
CPCC07C41/26C07C45/64C07C67/31C07B41/02C07C43/23C07C49/255C07C69/712Y02P20/52
Inventor 房立真朱润青孙倩倩杨晓丽李洛豪李静张涛高庆贺王亚坤周平鑫
Owner XINXIANG MEDICAL UNIV
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