Synthesis method of medical midbodies of para(ortho)-hydroxybenzoic acetone

A technology of o-hydroxyphenylacetone and hydroxyphenylacetone, which is applied in the field of synthesis of pharmaceutical intermediates p-hydroxyphenylacetone and o-hydroxyphenylacetone, can solve problems such as difficulty in obtaining raw materials, and achieves low production cost and easy industrialization , The effect of low process cost

Inactive Publication Date: 2009-09-30
CHANGZHOU RUIMING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] All there is the defective that raw material is not easy to obtain in above two kinds of methods

Method used

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  • Synthesis method of medical midbodies of para(ortho)-hydroxybenzoic acetone
  • Synthesis method of medical midbodies of para(ortho)-hydroxybenzoic acetone
  • Synthesis method of medical midbodies of para(ortho)-hydroxybenzoic acetone

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Experimental program
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Embodiment 1

[0020] Add 47 grams of p-methoxyphenylacetone, 100 milliliters of 48% hydrobromic acid, and 200 milliliters of glacial acetic acid in a 1000 milliliter three-necked flask, slowly heat up to reflux, TLC tracking (developer: petroleum ether: ethyl acetate=4: 1) Stop the reaction after reacting to the point where there is no raw material, cool and concentrate under reduced pressure, then add 100 ml of water, then extract the water phase 4 times with 100 ml of ethyl acetate, combine the organic layers, wash the ester layer with saturated aqueous sodium chloride solution, After drying overnight with anhydrous sodium sulfate, after concentrating and refining, 35.5 grams of the product were obtained, with a yield of 82.6%, and the gas phase detection result: the content was greater than 99.5%. Properties: light yellow crystal, melting point 34-35 degrees, bp177 degrees / 11mmHg.

Embodiment 2

[0022] Add 47 grams (0.287mol) of p-methoxyphenylacetone in a 1000 milliliter three-necked flask, 200 milliliters of 36% concentrated hydrochloric acid, 200 milliliters of glacial acetic acid, slowly warming up to reflux, TLC traces (developing agent: sherwood oil: ethyl acetate =4: 1) Stop the reaction after reacting to the point of no raw material, cool and concentrate under reduced pressure, then add 100 ml of water, then extract the aqueous phase with 100 ml of ethyl acetate for 4 times, combine the organic layers, and wash with saturated aqueous sodium chloride solution The ester layer was dried overnight with anhydrous sodium sulfate, concentrated and then refined to obtain 30.2 g of the product with a yield of 70.2%. Properties: light yellow crystal, melting point 34-35 degrees, bp177 degrees / 11mmHg.

Embodiment 3

[0024] Add 47 grams (0.287mol) of o-methoxyphenylacetone in a 1000 milliliter three-necked flask, 100 milliliters of 48% hydrobromic acid, 200 milliliters of glacial acetic acid, slowly warming up to reflux, TLC tracking (developing agent: sherwood oil: ethyl acetate Ester=4:1) Stop the reaction after reacting to the point where there is no raw material, cool and concentrate under reduced pressure, then add 100 ml of water, then extract the aqueous phase with 100 ml of ethyl acetate for 4 times, combine the organic layers, and wash with saturated aqueous sodium chloride solution The ester layer was washed, dried overnight with anhydrous sodium sulfate, concentrated and refined to obtain 31.6 g of light yellow crystals, with a yield of 73.5%.

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Abstract

The invention relates to the field of medical chemical engineering, in particular to a synthesis method of medical midbodies of para-hydroxybenzoic acetone and ortho-hydroxybenzoic acetone. The method comprises the following steps: adding para-methoxybenzoic acetone or ortho-methoxybenzoic acetone to solvent; adding an acidolysis agent for acidolysis refluence; concentrating after a reaction; adding water into concentrate for dissolution; using ethyl acetate to extract; and concentrating and rectifying an extracting solution. The invention has easily obtainable raw materials, mild reaction conditions, simple reaction procedures, high product content larger than 99 percent, product yield larger than 70 percent and low production cost and is suitable for industrialized mass production.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a method for synthesizing pharmaceutical intermediates p-hydroxyphenylacetone and o-hydroxyphenylacetone. Background technique [0002] p-hydroxyphenylacetone (CAS: 770-39-8), o-hydroxyphenylacetone (CAS: 3100-05-5) are important pharmaceutical and chemical intermediates, used to synthesize pharmaceutical and chemical intermediates such as 3-bromo- 4-hydroxyphenylacetone, anti-asthma drug fenoterol and various new adrenergic receptor antagonist drugs (Bioorganic Medicinal Chemistry Letters, 2006, 16(21): 5691-5694. Bioorganic Medicinal Chemistry Letters, 2003, 13 (16): 2687-2692.). [0003] JP 60222437 discloses a kind of synthetic method of it, and reaction formula is: [0004] [0005] Literature (Tetrahedron Letters, 1983, 24 (4): 417-18.) also discloses a kind of synthetic method of it, and reaction formula is: [0006] [0007] The synthesis of o-hydrox...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/245C07C45/64
Inventor 史为民操锋
Owner CHANGZHOU RUIMING PHARMA
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