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Preparation method of D-(-)-formyl mandelate chloride

A technology of formyl mandelic acid and formyl mandelic acid is applied in the preparation field of D--O-formyl mandelic acid chloride, can solve the problems such as inability to apply mechanically, waste of raw material formic acid, and no cost saving, and achieves easy operation, The effect of saving formic acid and easy absorption

Pending Publication Date: 2021-09-07
JIANGXI KEYUAN BIOPHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reclaimed formic acid mentioned in this invention is recycled, and the reclaimed formic acid contains a large amount of water and cannot be used mechanically, and does not save costs, resulting in a great waste of raw formic acid

Method used

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  • Preparation method of D-(-)-formyl mandelate chloride
  • Preparation method of D-(-)-formyl mandelate chloride
  • Preparation method of D-(-)-formyl mandelate chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Table 1 Synthesis of formylmandelic acid feed ratio

[0034]

[0035] Add 300 g of D-mandelic acid, 100 g of formic acid, and 300 g of methylene chloride into a 2000 ml four-necked bottle, and stir at room temperature for half an hour to dissolve it.

[0036] After dissolving, add 5g of activated carbon, lower the temperature to 0-10°C, then add a mixed solution of 195g of solid light and 300g of dichloromethane dropwise, at a temperature of 0-10°C, during which hydrogen chloride gas is precipitated, and the dropping time is 3h.

[0037] After the dropwise addition, keep the temperature at 10-20°C for 5 hours, filter the activated carbon, and recover dichloromethane and excess formic acid under normal pressure. 350-360 g of colorless viscous D(-) formylmandelic acid liquid was obtained.

Embodiment 2

[0039] Table 2 synthesis of D-formyl mandelic acid chloride feed ratio

[0040]

[0041] Put the D(-)formylmandelic acid crude product obtained in the first step of distillation into a 2000ml four-necked bottle, then add 300g of dichloromethane and 5g of activated carbon into the four-necked bottle, and dropwise add 220g of solid light at 10-20°C The dichloromethane solution was added dropwise for 5 hours, and hydrogen chloride gas was precipitated in the middle. After the dropwise addition, keep the temperature at 15-20° C. for 1 hour, and slowly raise the temperature to reflux. After refluxing for 5 hours, cool down and filter out the activated carbon, recover dichloromethane, and then place the residue under a mechanical pump and distill the product under a 1mHg vacuum to obtain a colorless and transparent D(-)formylmandelic acid chloride. The obtained D(-)formylmandelic acid chloride is 380-390g, the detection content is more than 99%, ee99%.

Embodiment 3

[0043] Put 300 g (1.97 mol) of D-mandelic acid, 100 g (2.17 mol) of formic acid, and 300 g of methylene chloride into a 2000 ml four-necked bottle, and stir at room temperature for half an hour to dissolve it.

[0044] After dissolving, add 5 g of activated carbon, lower the temperature to 0-10° C., and then add the dichloromethane solution of solid light dropwise into the solution. The amount of solid light added is shown in Table 3. The dropping temperature is 0-10°C, and hydrogen chloride gas is precipitated in between, and the dropping time is 3 hours.

[0045] After the dropwise addition, keep the temperature at 10-20°C for 5 hours, filter the activated carbon, and recover dichloromethane and excess formic acid under normal pressure. A colorless viscous D(-)formylmandelic acid liquid was obtained.

[0046]It is calculated that when the amount of solid light added is 1.2mol, 1mol, 0.6mol, 0.4mol respectively, the conversion rate of D-mandelic acid reaches 99.9%, 99.9%, 99...

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Abstract

According to the method, D-mandelic acid, dichloromethane and a slightly excessive amount of anhydrous formic acid are subjected to formylation reaction under the catalysis of activated carbon by using solid light as a dehydrating agent to obtain colorless viscous D (-) formyl mandelic acid, and the colorless viscous D (-) formyl mandelic acid is directly used for next-step reaction without being purified. Dichloromethane is added into the colorless sticky substance D (-) formyl mandelic acid for dissolving, an activated carbon catalyst is added, a light-reinforcing solution is dropwise added, heat preservation reaction is performed, and after the reaction is finished, dichloromethane is distilled and recovered to obtain colorless transparent liquid, namely D (-) formyl mandelate chloride. In the reaction, formaldehyde is added as the dehydrating agent so that the use of formaldehyde can be saved, the reaction is mild and environment-friendly, the reaction conversion rate and the product purity can be effectively improved, the production cost is effectively reduced, the operation is simple and convenient, and the industrial production is more facilitated.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and relates to a preparation method of D-(-)-O-formylmandelic acid chloride. Background technique [0002] D-(-)-O-formylmandelic acid chloride (D-FMC) is an important raw material for the synthesis of cephalosporins, cefnixime sodium and polymendolide sodium, and is also a chemical raw material. At present, the domestic traditional preparation of D-(-)-O-formylmandelic acid chloride widely adopts the formic acetic anhydride method, which uses sodium formate as a raw material, but will generate impurities of acetylmandelic acid chloride. It is not conducive to obtaining high-purity D-(-)-O-formylmandelic acid chloride. [0003] It is mentioned in the existing patent CN103319335A that using thionyl chloride as a dehydrating agent, formic acid and mandelic acid generate formylmandelic acid, and then chlorinated with thionyl chloride to generate formylmandelic acid chloride. A large a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/29C07C69/07C07C67/08
CPCC07C67/29C07C67/08C07B2200/07C07C69/07
Inventor 曹金辉刘建明宗匡曾鹏喻海亮陈文欢
Owner JIANGXI KEYUAN BIOPHARM