Method synthesizing 4, 4, 4-trifluoro butanol

A technology of trifluorobutanol and a synthesis method, which is applied in the directions of hydrolysis preparation, organic chemistry, etc., can solve the problems of low yield and high price of lithium aluminum hydride, and achieve the effects of short process route, favorable industrial production and mild reaction conditions

Active Publication Date: 2013-08-28
XIAN CAIJING OPTO ELECTRICAL SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The used reagent lithium aluminum hydride ...

Method used

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  • Method synthesizing 4, 4, 4-trifluoro butanol
  • Method synthesizing 4, 4, 4-trifluoro butanol
  • Method synthesizing 4, 4, 4-trifluoro butanol

Examples

Experimental program
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Embodiment 1

[0040] The synthetic steps of 4,4,4-trifluorobutanol are as follows:

[0041]Step 1: Add 200g (1.6mol) 2-bromoethanol, 12.0g (0.048mol) pyridinium p-toluenesulfonate and 400mL dichloromethane into a 1000mL three-necked flask, add 201.6g ( 2.4mol) 3,4-dihydropyran, keep the temperature at 20-30°C and continue the reaction for 1 hour after the dropwise addition. After the reaction of the raw material 2-bromoethanol is completed by gas chromatography, add 200mL water to the system, and let it stand for separation. liquid, the organic phase was washed twice with water, dried over anhydrous magnesium sulfate, the desiccant was filtered off, the solvent was evaporated by a rotary evaporator under reduced pressure, the remaining liquid was distilled under reduced pressure, and fractions at 98-102°C were collected (at a pressure of 3000Pa) to obtain 301.2 g of a transparent liquid, namely the 2-(2-bromoethoxy)tetrahydro-2H-pyran, with a gas chromatography content of 98.9% and a yield ...

Embodiment 2

[0049] The preparation process is the same as in Example 1, except that:

[0050] The catalyst in step 1 is p-toluenesulfonic acid, the molar ratio of 2-bromoethanol to 3,4-dihydropyran is 1:3, and the yield in step 1 is 89.6%;

[0051] In step 2, the molar ratio of 2-(2-bromoethoxy)tetrahydro-2H-pyran to magnesium powder is 1:2;

[0052] The catalyst in step 3 is dilithium tetrachloroketone, and the catalyst dosage is 5% of the molar weight of 2,2,2-trifluoroethyl methanesulfonate, and the yield in step 3 is 54.6%;

[0053] The catalyst in step 4 is Dowex-50 (H type) cation exchange resin, and the catalyst dosage is 1 to 10 based on the mass of 2-(4,4,4-trifluorobutoxy)tetrahydro-2H-pyran %, preferably 10%, step 4 yield is 65%, product gas chromatography content 98.5%.

Embodiment 3

[0055] The preparation process is the same as in Example 1, except that:

[0056] In step 1, the molar ratio of 2-bromoethanol to 3,4-dihydropyran is 1:1, and the yield in step 1 is 86.2%;

[0057] In step 2, the molar ratio of 2-(2-bromoethoxy)tetrahydro-2H-pyran to magnesium powder is 1:1;

[0058] The catalyst in step 3 is dilithium tetrachloroketone, and the catalyst dosage is 1% of the molar weight of 2,2,2-trifluoroethyl methanesulfonate, and the yield in step 3 is 50.1%;

[0059] The solvent in step 4 is methanol, the catalyst is Dowex-50 (H type) cation exchange resin, and the amount of catalyst is based on the mass of 2-(4,4,4-trifluorobutoxy)tetrahydro-2H-pyran 1%, step 4 yield is 60%, product gas chromatography content 98.5%.

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Abstract

The invention discloses a method for synthesizing 4, 4, 4-trifluoro butanol, wherein the method comprises: using 2-bromoethanol as a raw material, protecting a alcoholic hydroxyl group with 3,4-dihydro pyrans, preparing a Grignard reagent, carrying out coupling reaction of the Grignard reagent with 2,2,2-trifluoro ethyl methanesulfonates, and finally obtaining 4,4,4-trifluoro butanol by deprotection reaction. The method has advantages of short technology route, mild reaction condition, cheap and easily available raw materials, high reaction overall yield and low production cost, is in favor of industrialization production, and avoids usage of expensive raw materials like trifluoro butyric acid and lithium aluminium hydride.

Description

technical field [0001] The invention belongs to the preparation of fluorine compounds, in particular to a synthesis method of 4,4,4-trifluorobutanol. Background technique [0002] 4,4,4-Trifluorobutanol is an important organic intermediate, which is widely used in the fields of medicine, liquid crystal and organic semiconductor. U.S. patents US2005009838 and US4563525 respectively reported the application of 4,4,4-trifluorobutanol in the preparation of protease inhibitors and central nervous system inhibitors. Merck company used trifluorobutanol as raw material in German patent DE4415882 to prepare A series of liquid crystal compounds containing 4,4,4-trifluorobutyl ether. Existing 4,4,4-trifluorobutanol preparation method mainly contains following several kinds: [0003] 1) Preparation from 1,1,1-trichloro-2,2,2-trifluoroethane (CFC113a) [0004] U.S. Patent US2002095059 uses 1,1,1-trichloro-2,2,2-trifluoroethane as a raw material, and reacts with tert-butyl propylene et...

Claims

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Application Information

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IPC IPC(8): C07C31/38C07C29/10
Inventor 高嫒嫒胡明刚杜渭松刘建韬别国军
Owner XIAN CAIJING OPTO ELECTRICAL SCI & TECH
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