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Method for synthesizing 2,2,4,4-tetramethyl-1,3-cyclobutanediol

A cyclobutanediol and synthesis method technology, applied in 2 fields, can solve the problems of high cost of raw materials, harsh requirements on reaction vessel and operating conditions, and low yield of cyclocondensation

Inactive Publication Date: 2014-04-02
NANJING NANOEAST BIOTECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These processes have strict requirements on reaction vessels and operating conditions, high raw material costs, and low cyclocondensation yields, which are not conducive to industrial production.

Method used

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  • Method for synthesizing 2,2,4,4-tetramethyl-1,3-cyclobutanediol
  • Method for synthesizing 2,2,4,4-tetramethyl-1,3-cyclobutanediol
  • Method for synthesizing 2,2,4,4-tetramethyl-1,3-cyclobutanediol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] In a three-necked flask equipped with a condenser, 5.3g (0.05mol) isobutyryl chloride and 40mL ether were added, and 8.6g (0.085mol) triethylamine was added under stirring evenly. The system was heated to reflux and reacted for 15h, and then the system was cooled. Wash with dilute hydrochloric acid until the white turbidity is dissolved and separate. The aqueous layer was extracted with ether, the organic phases were combined, and part of the solvent was evaporated under reduced pressure to obtain a mixed solution of a white intermediate.

[0016] Add the above-mentioned mixture containing intermediates to a three-necked flask, then add it to a 50mL methanol and 50mL water system, adjust the pH of the solution to alkaline with 10% NaOH, and add 2g (0.053mol) in batches under ice bath conditions NaBH 4 After the addition, react for 4h at room temperature, quench with dilute hydrochloric acid, spin-dry the reaction solution, and extract with 100mL absolute ethanol. The extra...

Embodiment 2

[0018] In a three-necked flask equipped with a condenser, 5.3g (0.05mol) isobutyryl chloride and 40mL propyl ether were added, and 8.6g (0.085mol) triethylamine was added under stirring evenly. The system was heated to reflux and reacted for 15h, and then the system was cooled. Wash with dilute hydrochloric acid until the white turbidity is dissolved and separate. The aqueous layer was extracted with propyl ether, the organic phases were combined, and part of the organic solvent was evaporated under reduced pressure to obtain a mixed solution in which a white intermediate was precipitated.

[0019] Add the above-mentioned mixed solution containing intermediates into a three-necked flask, then add it to 70mL methanol and 30mL water system, adjust the pH of the solution to alkaline with 10% NaOH, add 2g (0.053mol) in batches under ice bath conditions NaBH 4 After the addition, react for 4h at room temperature, quench with dilute hydrochloric acid, spin-dry the reaction solution, an...

Embodiment 3

[0021] Add 5.3g (0.05mol) isobutyryl chloride and 40mL ethylene glycol diethyl ether into a three-necked flask equipped with a condenser, add 8.6g (0.085mol) triethylamine under stirring evenly, and then heat and reflux for 15h to cool the system. Wash with dilute hydrochloric acid until the white turbidity dissolves, separate the layers, extract the aqueous layer with ethylene glycol diethyl ether, combine the organic phases, and evaporate part of the solvent under reduced pressure to obtain a mixture of precipitated white intermediates.

[0022] Add the above-mentioned mixture containing intermediates to a three-necked flask, and then add it to the 30mL methanol and 70mL water system, adjust the pH of the solution to alkaline with 10% NaOH, add 2g (0.053mol) in batches under ice bath conditions NaBH 4 After the addition, react for 4h at room temperature, quench with dilute hydrochloric acid, spin-dry the reaction solution, and extract with 100mL absolute ethanol. The extract is ...

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Abstract

The invention discloses a method for preparing 2,2,4,4-tetramethyl-1,3-cyclobutanediol. Iso-butyryl chloride used as a raw material is stirred evenly in ether solvent, triethylamine is added, reflux reaction is carried out for 13-16h, diluted hydrochloric acid is used for washing, pressure is reduced to remove solvent to obtain intermediate 2,2,4,4-tetramethyl-1,3-cyclobutanedione, the intermediate is dissolved in mixed solvent of methyl alcohol and water, NaOH is used for regulating pH value to be alkaline, quantitative NaBH4 is added in batches under an ice-bath condition, the reaction is performed for 3-5h at normal temperature, diluted hydrochloric acid is used for quenching, solvent is removed, absolute ethyl alcohol is used for extraction, after ethyl alcohol is removed through rotary evaporation, water is used for extraction, and finally, the water is removed to obtain 2,2,4,4-tetramethyl-1,3-cyclobutanediol. The method has simple equipment requirement, mild operation condition, low cost and high product purity, and is suitable for industrial production.

Description

Technical field [0001] The invention relates to a method for 2,2,4,4-tetramethyl-1,3-cyclobutanediol, and belongs to the field of organic medicine synthesis and technology. Background technique [0002] 2,2,4,4-Tetramethyl-1,3-cyclobutadiol, English name: 2,2,4,4-Tetramethyl-1,3-cyclobutadiol, CAS number: 3010-96-6, molecular formula : C 8 H 16 O 2 , Molecular weight: 144.21, melting point: 126-129°C, boiling point: 210-215°C. 2,2,4,4-Tetramethyl-1,3-cyclobutanediol can enhance the effectiveness of antibacterial agents commonly used in coatings and latex dispersion media. It can also be used alone or as part of a preservative system. It is stable in the water phase while reducing the use of traditional preservatives. The shelf life of the antibacterial system can be extended through synergy. [0003] There are few domestic reports on the preparation method of 2,2,4,4-tetramethyl-1,3-cyclobutanediol. Cyclic diketones are used in Al 2 O 3 The surface is loaded with Ru (or Co, Ni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C35/04C07C29/143
CPCC07C29/143C07C45/46C07C2601/04
Inventor 韩国志庞峰飞王普李郭成王建国
Owner NANJING NANOEAST BIOTECH
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