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Synthesis method of R-2-fluorine methyl lactate

A kind of technology of methyl fluorolactate and synthetic method, applied in the field of synthetic route of industrial production, can solve problems such as not mentioned

Active Publication Date: 2015-07-15
浙江中硝康鹏化学有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, in the current mainstream synthesis technology, especially in the above synthesis methods, there is no mention of how to treat the waste water after distilling out the product and recovering the organic base when synthesizing R-2-fluoromethyl lactate

Method used

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  • Synthesis method of R-2-fluorine methyl lactate
  • Synthesis method of R-2-fluorine methyl lactate
  • Synthesis method of R-2-fluorine methyl lactate

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preparation example Construction

[0030] The invention relates to a method for synthesizing R-2-fluoromethyl lactate. This method is to obtain R-2-fluorolactate methyl ester by S-methyl lactate in the presence of an organic base, by selectively feeding or not feeding hydrogen fluoride gas, fluorinating with sulfuryl fluoride, and then short-distilling and rectifying. Organic bases can be recovered and reused without reducing reactivity. The method has high yield and high ee value, only produces few "three wastes", and the raw materials are cheap and easy to obtain.

[0031] Compound R-2-fluoromethyl lactate of the present invention takes S-methyl lactate as a raw material, and it is speculated that it is obtained by the following mechanism:

[0032]

[0033] A preferred embodiment of the present invention is,

[0034] The distillation residue is added with an inorganic base to recover N,N-dimethylaniline, which can be reused without reducing the reactivity.

[0035] Specifically, the synthetic method of ...

Embodiment 1

[0062] The following examples will help to further understand the present invention, but do not limit the content of the present invention.

[0063] Step 1: Reaction and purification of R-2-fluoromethyl lactate

[0064] Add 1249.2g of S-methyl lactate and 2669g of tri-n-butylamine into a 5L reaction flask, cool down to -10°C, keep warm at -10-0°C and feed 1286g of sulfonyl fluoride gas until the reaction of S-methyl lactate is complete. The crude product was distilled off and rectified to obtain 1056.5 g of methyl R-2-fluorolactate with a yield of 83%. The content determined by gas chromatography was 99.8%, and the ee value was 97.24%. The residue of the kettle is 3945g.

[0065] The recovery of step two n-tributylamine one

[0066] 3945g of the still residue obtained in step 1 was heated to 60°C, and 4160g of 15% sodium hydroxide solution was added dropwise. After the dropwise addition was completed, the liquid was separated after heat preservation to obtain 5445 g of the ...

Embodiment 2-7

[0072] The consumption of organic base and S-methyl lactate is changed, others are the same as Example 1, and the results are shown in Table 1

[0073] Table 1:

[0074] Example

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Abstract

The invention discloses a synthesis method of R-2-fluorine methyl lactate. The method comprises the following steps: (1) in the presence of organic base, fluorinating S-methyl lactate by virtue of a fluorinating reagent so as to obtain a crude R-2-fluorine methyl lactate product, and rectifying the crude product so as to obtain R-2-fluorine methyl lactate and kettle residue; (2) mixing the kettle residue with a solution containing the inorganic base and a separating liquid to obtain an aqueous phase and an organic phase, and recovering the organic base from the organic phase; and (3) repeating the step (1) with the recovered organic base so as to obtain the R-2-fluorine methyl lactate.

Description

technical field [0001] The invention relates to a method for producing highly optically active methyl R-2-fluorolactate, in particular to a synthetic route that reduces environmental pollution, has high yield and ee value, and is suitable for industrial production. Background technique [0002] At present, there are three main methods for the synthesis of methyl R-2-fluorolactate: [0003] One is to use S-methyl lactate as a raw material, firstly treated with thionyl chloride, and then treated with fluoride to obtain the product [0004] [0005] The second is to use S-methyl lactate as a raw material, firstly treat it with methanesulfonyl chloride, and then treat it with fluoride to obtain the product (DE-A4131242; EP 1 671 939); [0006] [0007] The third is to use S-methyl lactate as a raw material, which is treated with sulfonyl fluoride, and then refined to obtain the product (WO2008 / 090755); [0008] [0009] The R-2-fluoromethyl lactate that can be obtaine...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/63C07C67/307
CPCC07C67/307C07C69/63
Inventor 孙梁杜友兴江向阳
Owner 浙江中硝康鹏化学有限公司
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