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An avenantha alkaloid and a preparation process technology, applied in the field of cosmetic chemistry, can solve the problems of difficulty in recovering and applying thionyl chloride, not easy to promote in industrialization, increase production and processing costs, etc., so as to reduce production and processing costs, inhibit hydrolysis, and reduce emissions. amount of effect
Active Publication Date: 2021-06-11
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY +2
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[0007] CN106631865A uses organic acid as raw material, thionyl chloride as acyl chloride reagent, anthranilic acid ammonolysis, and hydrolysis to obtain a class of oat alkaloids. This process uses excess thionyl chloride as acyl chloride r
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Embodiment 1
[0046] The preparation technology of dihydrooat alkaloid D comprises the steps:
[0047] (1) Preparation of p-acetoxyphenylpropionic acid
[0048] Add 105 g (2.625 mol) of sodium hydroxide into a 5 L reactor, stir and dissolve in 320 mL of water, add 166 g (1 mol) of p-hydroxyphenylpropionic acid, and stir to dissolve. 224 g of acetic anhydride (2.2 mol) was added dropwise in an ice bath (-5-0°C). During the dropwise addition, the solution was a milky white suspension, and stirred at room temperature for 14 hours. The pH of the solution was adjusted to 4.4 with hydrochloric acid, extracted with ethyl acetate, washed with water, and dried to obtain 204.1 g of crude p-acetoxyphenylpropionic acid.
[0049] The above crude p-acetoxyphenylpropionic acid was dissolved in 150mL of toluene, connected to the water separator, azeotropic distillation for 2h, 120mL of toluene was distilled off, recycled, and dried to obtain 199.2g of p-acetoxyphenylpropionic acid, with a yield of 95.7%. ...
Embodiment 2
[0066] The preparation technology of dihydrooat alkaloid D comprises the steps:
[0067] (1) Preparation of p-acetoxyphenylpropionic acid
[0068] Add 100.8g (2.52mol) of sodium hydroxide into a 5L reactor, stir and dissolve in 320mL of water, add 166g (1mol) of p-hydroxyphenylpropionic acid, stir and dissolve. 214.4 g of acetic anhydride (2.1 mol) was added dropwise in an ice bath (-5-0°C). During the dropwise addition, the solution was a milky white suspension, and stirred at room temperature for 14 hours. The pH of the solution was adjusted to 4.3 with hydrochloric acid, extracted with ethyl acetate, washed with water, and dried to obtain 203.5 g of crude p-acetoxyphenylpropionic acid.
[0069] The above crude p-acetoxyphenylpropionic acid was dissolved in 150mL of toluene, connected to the water separator, azeotropic distillation for 2h, 115mL of toluene was distilled off, recycled, and dried to obtain 199.7g of p-acetoxyphenylpropionic acid, with a yield of 96.0%.
[00...
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Abstract
The invention relates to a preparation process of dihydrooat alkaloid D. The preparation process comprises the following three steps: phenolic hydroxyl group protection, acylating chlorination and amidation, and hydrolysis deprotection, wherein p-hydroxyphenylpropionic acid and acetic anhydride are used as raw materials to obtain p-acetoxyphenylpropionic acid; 2-[(p-acetoxy) benzene propionylamino] methyl benzoate is obtained by taking a chlorinated solvent as a reaction medium, taking a slightly excessive amount of thionyl chloride as an acylation reagent and taking magnesium oxide or calcium oxide as an acid-binding agent; hydrolyzing is carried out by adopting a sodium hydroxide solution, and acidifying is carried out by adopting a hydrogen chloride alcoholic solution to obtain the dihydrooat alkaloid D. According to the process, phenolic hydroxyl groups are protected, self-polymerization of a substrate is avoided, and generation of by-products is reduced; alkaline-earth metal oxide is selected as an acid-binding agent, material overflow is avoided, a hydrogen chloride alcoholic solution is used for replacing hydrochloric acid for acidification, a large amount of waste acid and waste water are avoided, toxic and harmful solvents are not used, and the method is economical and environmentally friendly. The process is easy to control, the yield is high, byproducts are few, and the method is suitable for industrial production of the dihydrooat alkaloid D.
Description
technical field [0001] The invention relates to a preparation process of dihydrooat alkaloid D, which belongs to the field of cosmetic chemistry. Background technique [0002] Dihydroavenous alkaloid D is formed by linking cinnamic acid derivatives and anthranilic acid through an amide bond (-CO-NH-). It contains azophenolic acid structure and has various biological activities such as antioxidant, anti-inflammatory and antipruritic. , is widely used in cosmetics, such as creams, repairing masks, shampoos and insect bites; it can also be added to medical ointments to reduce inflammation and erythema, and effectively improve skin itching symptoms. [0003] At present, there are few reports on the synthesis of dihydroavenous alkaloid D. WO2005016870 uses p-hydroxyphenylpropionic acid and anthranilic acid as raw materials, N,N-carbonyldiimidazole as a condensation agent, and pyridine as an acid-binding agent through amide condensation. Dihydroavenous alkaloid D was prepared for...
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