Preparation method of dihydrooat alkaloid

A technology of oat alkaloids and dihydrogen, which is applied in the field of preparation of dihydrooat alkaloids, can solve the problems of being unsuitable for industrial production, long synthesis route, and large environmental pollution, and achieves convenience for large-scale production, short preparation process steps, The effect of low solvent toxicity

Pending Publication Date: 2022-05-13
河南旭瑞新材料科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] The purpose of the present invention is to overcome the deficiencies in the prior art, provide a kind of preparation method of dihydrooat alkaloids, solve the existin...

Method used

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  • Preparation method of dihydrooat alkaloid
  • Preparation method of dihydrooat alkaloid
  • Preparation method of dihydrooat alkaloid

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Embodiment 1

[0038] A preparation method of dihydrooat alkaloids, comprising the steps of:

[0039] S1. Preparation of methyl p-hydroxyphenylpropionate: In a 250mL three-neck flask, add p-hydroxyphenylpropionic acid (50g, 1.0eq), 150mL of methanol and 5g of concentrated sulfuric acid in sequence, heat up and reflux for 6-8 hours, and monitor the end of the reaction by TLC Finally, excess methanol was removed to obtain a brown oil, 100 mL of dichloromethane was added to the oil, and then 50 mL of water was added to separate the organic phase, which was then dried with saturated sodium bicarbonate solution, anhydrous magnesium sulfate, and concentrated 53 g of oil was obtained, the HPLC purity was greater than 98%, and the oil was recrystallized from an ethanol / water mixed solvent to obtain 48 g of off-white crystal powder (methyl p-hydroxyphenylpropionate), with a melting point of 38-39° C. and a yield of 89.2%;

[0040] S2. Preparation of crude dihydrooat alkaloids: In a 250mL three-necked...

Embodiment 2

[0046] A preparation method of dihydrooat alkaloids, comprising the steps of:

[0047] S1. Preparation of ethyl p-hydroxyphenylpropionate: In a 250mL three-necked flask, add p-hydroxyphenylpropionic acid (50g, 1.0eq), 150mL of absolute ethanol and 5g of concentrated sulfuric acid in sequence, and heat up and reflux for 6-8h, monitor by TLC After the reaction, excess ethanol was removed to obtain a brown oil, which was extracted by adding petroleum ether, followed by drying with saturated sodium bicarbonate solution, anhydrous magnesium sulfate, and concentrating to obtain 53.1 g of oil with an HPLC purity of 99.6 %, yield 91.5%;

[0048] S2, the preparation of dihydrooat alkaloid crude product: in 250mL there-necked flask, add ethyl p-hydroxyphenylpropionate (50g, 1.0eq), sulfolane (100mL, 2V), anthranilic acid (35g, 1.0eq) and Concentrated sulfuric acid (5g, 0.17X), heat up to 130-140°C, keep warm for 6-8h; then cool down to below 70°C, slowly add 200-400mL of water, and the...

Embodiment 3

[0051] A preparation method of dihydrooat alkaloids, comprising the steps of:

[0052] S1. Preparation of methyl p-hydroxyphenylpropionate: In a 250mL three-necked flask, add p-hydroxyphenylpropionic acid (50g, 1.0eq), 100mL of methanol and 4.75g of concentrated sulfuric acid in sequence, heat and reflux for 6-8 hours, and monitor the reaction by TLC After the end, remove excess methanol to obtain a brown oil, add 100mL of dichloromethane to the oil, then add 50mL of water, separate the organic phase, and then dry the organic phase with saturated sodium bicarbonate solution, anhydrous magnesium sulfate, and concentrate Finally, 53g of oily matter was obtained, and the HPLC purity was greater than 98%. The oily matter was recrystallized from an ethanol / water mixed solvent to obtain 48g of off-white crystal powder (methyl p-hydroxyphenylpropionate), with a melting point of 38-39°C and a yield of 89.2%. ;

[0053] S2. Preparation of crude dihydrooat alkaloids: In a 250mL three-n...

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Abstract

The invention discloses a preparation method of dihydro-oat alkaloid, which comprises the following steps: S1, preparation of p-hydroxyphenyl propionate, S2, preparation of a dihydro-oat alkaloid crude product, and S3, preparation of a dihydro-oat alkaloid competitive product.The amine ester exchange catalyst is preferably concentrated sulfuric acid and p-toluenesulfonic acid, so that the reaction is more facilitated; although the raw material has an aniline structure and can form aniline salt at low temperature, when the temperature is higher than 120 DEG C, the unstable aniline salt can be dissociated and continuously participates in the reaction, so that the conversion rate of the raw material is increased; the amine ester exchange solvent is preferably DMSO (dimethylsulfoxide) and sulfolane, the two solvents have the properties of high boiling point and good solubility, and meanwhile, the solvents are low in toxicity, have water solubility, are simple in post-treatment, and are convenient for refining and purifying a dihydrooat alkaloid crude product; meanwhile, the preparation process is short in step, the yield of the two-step reaction is 80% or above, and industrial large-scale production is facilitated.

Description

technical field [0001] The invention belongs to the technical field of cosmetics preparation, and in particular relates to a preparation method of dihydroavenous alkaloids. Background technique [0002] Dihydrooat alkaloids, also known as hydroxyphenylpropanamide benzoic acid, have rapid anti-inflammatory and antipruritic activities, and are widely used in skin care products and cosmetics. This product can exert multiple effects such as antihistamine, anti-oxidation, anti-irritation, anti-inflammation, and improvement of erythema. It also has good effects in alleviating itching, irritation, and redness of sensitive skin. This product is a powerful non-steroidal anti-inflammatory and anti-itching natural ingredient, which has a potency comparable to that of hydrocortisone, but without any side effects of steroid hormones, and has broad market prospects. [0003] At present, regarding the synthesis of dihydroavenous alkaloids, in the world patent document WO2005016870, a trad...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C235/38C07C67/08C07C69/732B01J31/02
CPCC07C231/02C07C67/08B01J27/053B01J27/02B01J31/0225B01J35/0006B01J2231/49C07C235/38C07C69/732
Inventor 马可望王志刚周永增蒋腾飞
Owner 河南旭瑞新材料科技有限公司
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