Method for producing optical homochiral amygdalic acid

A technology of mandelic acid and methyl mandelic acid, which is applied in the field of chemical biosynthesis to produce optically pure chiral mandelic acid, and can solve the problems that the S-type synthesis has not been reported yet.

Inactive Publication Date: 2005-12-21
SHANDONG UNIV
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Problems solved by technology

According to reports, some countries in the world have been able to produce R-typ

Method used

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  • Method for producing optical homochiral amygdalic acid

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Embodiment 1

[0037] 1. Synthesis of benzoyl formate: Add 40mL (0.347moL) of benzoyl chloride, 20g (0.408moL) of NaCN, 10g (0.1moL) of CuCl, 8.5mL of xylene and 5mL of acetonitrile into a 250mL round-bottomed flask in sequence, and place at 130 °C and heated to reflux for 5 hours. Cool to room temperature after the reaction, filter with suction, and wash with xylene. The resulting filtrate was distilled under reduced pressure, and the fraction at 112-117°C (reduced pressure) was collected to obtain 18.6 g (0.142 moL) of benzoylnitrile, with a yield of 41%, and mp of 32°C.

[0038] Carefully add 10 mL of concentrated sulfuric acid to 30 mL of absolute ethanol dropwise, add 6.5 g of benzoyl nitrile, heat and reflux for 24 hours, after the reflux reaction is completed, distill the ethanol under reduced pressure, pour the concentrated solution into cold water at 0°C, and use Extracted with ethyl acetate, washed the organic layer with 5% sodium carbonate solution and water respectively, dried o...

Embodiment 2

[0050] 1. Synthesis of benzoyl formate: Add 80mL (0.694moL) of benzoyl chloride, 40g (0.816moL) of NaCN, 20g (0.2moL) of CuCl, 17mL of xylene and 10mL of acetonitrile into a round-bottomed flask in sequence, and heat at 130°C Reflux for 6 hours. Cool to room temperature after the reaction, filter with suction, and wash with xylene. The resulting filtrate was distilled under reduced pressure, and the fraction at 112-117°C (43mmHg) was collected to obtain 38.1g (0.29moL) of benzoylnitrile, with a yield of 42%, and mp32°C.

[0051] Carefully add 10mL of concentrated sulfuric acid to 30mL of absolute ethanol dropwise, add 7.1g of benzoyl nitrile, heat and reflux for 28 hours, after the reflux reaction is complete, evaporate the ethanol under reduced pressure, pour the concentrated solution into cold water at 5°C, and use Extract with ethyl acetate, wash the organic layer with 5% sodium carbonate solution and water respectively, dry over anhydrous sodium carbonate, distill off the...

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Abstract

This invention discloses a method for producing optical pure chiral mandelic acid. Use methyl benzoyl formate or the derivative of phenylglyoxylic acid as the bottom thing, the microorganism's cell of yeasts or mould whitlying etc. as catalyst, alternatively reduces the carbonyl in the bottom thing to the hydroxyl to get the chiral mandelic acid relying mainly on a kind of type (usually as R a type). This invention adopts chemistry-biology combination craft , with low cost, the chiral purity is high, easy to realize production for industrialization, it is easy to popularize and apply.

Description

(1) Technical field [0001] The invention relates to a method for producing mandelic acid, in particular to a chemical biosynthesis method for producing optically pure chiral mandelic acid, which belongs to the related fields of chemistry and biotransformation. (2) Background technology [0002] Mandelic acid and its derivatives are widely used in organic synthesis, and can be used as important intermediates of medicine and dyes, and can also be used as analytical reagents for testing zirconium and ketones. The annual demand at home and abroad is large, but at present several methods of synthesizing mandelic acid at home and abroad are not very ideal, for example: benzaldehyde is used as raw material through the addition of nitrile group to aldehyde group to obtain β-hydroxyphenylacetonitrile, and then in acidic Mandelic acid is hydrolyzed in an aqueous solution, and the yield of this method is low, only 50%-52%; and benzaldehyde is used as a raw material to prepare mandelic ...

Claims

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Application Information

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IPC IPC(8): C12P7/42
Inventor 吉爱国孙利民孟昭力
Owner SHANDONG UNIV
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