Paeonol(link:https://www.bloomtechz.com/synthetic-chemical/api-researching-only/paeonol-powder-cas-552-41-0.html) is white or yellowish shiny needle-like crystals, colorless needle-like crystals (ethanol), melting point 49°C-51°C, special smell, slightly spicy taste, easily soluble in ethanol and methanol, soluble in ether, Among acetone, benzene, chloroform and carbon disulfide, slightly soluble in water, soluble in hot water, insoluble in cold water, can volatilize with water vapor. Paeonol can be distilled with water vapor, and has a strong absorption in the ultraviolet region. At the wavelength of 274nm, the E (1% 1cm) is 862. Using this property, it can be measured by ultraviolet spectrophotometer. Paeonol is a natural organic compound with various biological activities and pharmacological effects. It is often used in the fields of traditional Chinese medicine and cosmetics, and has various biological activities and pharmacological effects. The following is a brief description of several common synthetic methods of Paeonol.
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1. Octanoic Acid Method:
This is a common method of synthesizing Paeonol. First, react propiophenone and aminophenol under acidic conditions to generate p-hydroxypropiophenone. Then, p-hydroxyacetophenone is reacted with bromoacetic acid to generate p-hydroxyacetophenone. Next, reacting p-hydroxyacetophenone with a basic solution such as sodium hydroxide produces substrate migration to produce p-hydroxyacrylate. Finally, react p-hydroxyacrylate with octanoic acid under acidic conditions to generate Paeonol. The detailed steps and their chemical equations are as follows:
The first step: generate 4-Hydroxyphenylacetone (4-Hydroxyphenylacetone).
Reaction equation:
C9H10O + aminophenol → C9H10O2 + CO2
Under acidic conditions, propiophenone is acylated with aminophenol to produce p-hydroxypropiophenone.
The second step: generate p-hydroxyacetophenone (4-Hydroxyphenylacetophenone).
Reaction equation:
C9H10O2 + C2H3BrO2 → C8H8O2 + BrH
React p-hydroxyacetophenone with bromoacetic acid in an alkaline solvent to generate p-hydroxyacetophenone through acylation reaction.
The third step: generating 4-Hydroxyphenylpropenoate.
Reaction equation:
C8H8O2 + alkaline solution → p-hydroxyacrylate
React p-hydroxyacetophenone with an alkaline solution (such as sodium hydroxide), and a substrate migration reaction occurs to generate p-hydroxyacrylate.
Step 4: Generate Paeonol.
Reaction equation:
p-Hydroxyacrylate + C8H16O2 → C9H10O3
The p-hydroxy acrylate and octanoic acid are heated and reacted under acidic conditions to generate Paeonol through transesterification.
2. Reaction method of o-hydroxyanisole and benzyl alcohol:
Firstly, react o-hydroxyanisole and benzyl alcohol under acidic conditions to undergo a condensation reaction to generate m-hydroxybenzophenoxide. Then, m-hydroxybenzophenone was treated with sodium hydroxide to obtain stilbenzylphenol. Finally, stilbenephenols were converted to Paeonols by oxidation or lithium aluminum hydrogenation.
The octanoic acid method is a commonly used method for the synthesis of Paeonol. The following are the detailed steps of the octanoic acid method and its chemical equation:
3. Catechol and acetylacetone reaction method:
Firstly, catechol and acetylacetone are condensed through Alder-ene reaction to generate condensation products. Then, the cyclic lactonization reaction is carried out by acid catalysis or base catalysis to generate Paeonol.
Detailed steps and their chemical equations:
The first step: generate 2-hydroxy-3-phenylpropanone (2-Hydroxy-3-phenylpropanone).
Reaction equation:
C6H6O2 + C5H8O2 → 2-hydroxy-3-phenylacetone
Under acidic conditions, catechol is acylated with acetylacetone to generate 2-hydroxy-3-phenylacetone.
The second step: generate 4-hydroxy-2-methoxybenzaldehyde (4-Hydroxy-2-methoxybenzaldehyde).
Reaction equation:
2-Hydroxy-3-phenylacetone + ligand group → C8H8O3
2-Hydroxy-3-phenylacetone is reacted with a suitable ligand group, and a decarbonylation reaction occurs to generate 4-hydroxy-2-methoxybenzaldehyde.
Step 3: Generate Paeonol.
Reaction equation:
C8H8O3 + alkaline solution → C9H10O3
4-Hydroxy-2-methoxybenzaldehyde is reacted with an alkaline solution (such as sodium hydroxide) for formaldehyde removal to generate Paeonol.
4. Reaction method of o-aminophenol and maleic acid:
The reaction of o-aminophenol and maleic acid under alkaline conditions produces N-substituted maleimide. Next, react N-substituted maleimide with copper acetate catalyst to produce benzyl-substituted cyclopropenone. Finally, cyclopropenone is converted to Paeonol by hydrogenation.
Detailed steps and their chemical equations:
The first step: generate o-aminoacetophenone (2-Aminoacetophenone).
Reaction equation:
C6H7NO + C4H4O4 → C8H9NO
Under acidic conditions, react o-aminophenol with maleic acid to carry out acid anhydride acylation reaction to generate o-aminoacetophenone.
The second step: generate 4-hydroxy-2-methoxyacetophenone (4-Hydroxy-2-methoxyacetophenone).
Reaction equation:
C8H9NO + ligand group → C9H10O3
The o-aminoacetophenone is reacted with a suitable ligand group, and a deacylation reaction occurs to generate 4-hydroxy-2-methoxyacetophenone.
Step 3: Generate Paeonol.
Reaction equation:
C9H10O3 + alkaline solution → C9H10O3
4-Hydroxy-2-methoxyacetophenone reacts with alkaline solution (such as sodium hydroxide) to carry out deketone reaction to generate Paeonol.
It should be noted that the several methods listed above are only one of the common synthesis methods of Paeonol. According to different research purposes and conditions, there are many other methods for synthesizing Paeonol. In addition, these synthetic methods only provide approximate steps, and specific chemical reactions and operational details may vary from specific methods. If you are interested in the synthesis method of Paeonol, it is recommended to consult a professional organic synthetic chemist or consult relevant scientific literature to obtain more detailed and accurate information, or you can also send us an email, and we will reply you after consulting the scientific research staff .