Preparation method of (S)-(-)-1,1,2-triphenyl-1,2-ethanediol

Abstract

The invention relates to a preparation method of (S)-(-)-1,1,2-triphenyl-1,2-ethanediol. The preparation method is characterized by comprising the following steps: respectively dissolving methyl mandelate and phenyl magnesium bromide in solvents to prepare a methyl mandelate solution and a phenyl magnesium bromide solution; feeding the prepared methyl mandelate solution and the prepared phenyl magnesium bromide solution into a first micro-channel reactor respectively through a metering pump so as to perform main reaction, and enabling the reaction solution obtained after the reaction to directly flow into a second micro-channel reactor; feeding an acidic aqueous solution into the second micro-channel reactor through a metering pump so as to perform quenching reaction while the reaction solution flows into the second micro-channel reactor, layering the reaction solution obtained after the quenching reaction, and taking an organic phase; drying the organic phase, and then, performing vacuum concentration; and performing recrystallization with toluene to obtain the finished product (S)-(-)-1,1,2-triphenyl-1,2-ethanediol. The preparation method provided by the invention has the advantages of high yield and fast reaction.

Description

technical field [0001] The invention relates to a preparation method of (S)-(-)-1,1,2-triphenyl-1,2-ethanediol, in particular to the preparation of (S)-(-)- 1,1,2-Triphenyl-1,2-ethanediol method. Background technique [0002] (S)-(-)-1,1,2-triphenyl-1,2-ethylene glycol is an important intermediate for the preparation of optically active medicines, pesticides and functional materials, and its structural formula is as follows ( ): [0003] [0004] Its main synthesis method is: in the solution of Grignard reagent phenylmagnesium bromide, slowly add the solution of methyl mandelate dropwise at a certain temperature, keep warm for reaction, and obtain the product after post-processing, the reaction formula is as follows: [0005] [0006] The main references are 1. Advanced Synthesis and Catalysis; vol. 352; nb. 14-15; (2010); p. 2611-2620: 0-20°C under the protection of inert gas in tetrahydrofuran solvent, reaction for 50h, post-processing to obtain the product ; 2. ...

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Problems solved by technology

[0007] Most of the methods reported in the above literature use conventional reaction devices, most of the reaction time is very long, some even reach 50 hours, and the yield is generally not high. The reason for the analysis may be 1), due to the limitation of the mixing effect of the reactor, It is easy to produce incomplete reaction, resulting in a high proportion of impurity (S)-2-hydroxy-1,2-diphenylethanone in the product, and its structural formula is as follows (II); 2), after the reaction is completed, add When hydrochloric acid is quenched, the local acid concentration is too high, and dehydration side reactions occur, resulting in the generation of impurity 1,2,2-triphenylvinyl alcohol, whose structural formula is as follows ( )

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