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Method for synthesizing trans-1, 4-cyclic mono-tert-butyl adipate

A technology of cycloadipic acid and mono-tert-butyl ester is used in the synthesis of liquid crystal intermediates and the synthesis of trans-1,4-cycloadipic acid mono-tert-butyl ester, which can solve the problem of unsatisfactory product purity and reaction conversion rate. It is not high, the process is complicated, etc., to achieve the effect of simple operation, high purity and simple process

Active Publication Date: 2020-12-15
江苏创拓新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The method comprises four steps of chemical reactions; the process is complex, the flow process is long, the operation is cumbersome, and the yield is low (total yield about 24%)
[0008] Through research, the main reason for the low yield of the above synthesis method is that the yield of the first two steps of the chemical reaction is low, and the more internal reason is that the use of sodium hydroxide and methanol leads to a low reaction conversion rate.
In addition, the purity of the product obtained by the above synthetic method is still not ideal
[0009] The inventor has not yet found that trans-1,4-cyclohexanedioic acid is first esterified (reaction 1) to obtain trans-1,4-cyclohexanedioic acid bis-tert-butyl ester and then hydrolyzed (reaction 1) by fully searching the prior art. 2) Obtaining the report of mono-tert-butyl trans-1,4-cyclohexanedioate

Method used

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  • Method for synthesizing trans-1, 4-cyclic mono-tert-butyl adipate
  • Method for synthesizing trans-1, 4-cyclic mono-tert-butyl adipate
  • Method for synthesizing trans-1, 4-cyclic mono-tert-butyl adipate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1) Esterification reaction:

[0042] Put 5g of trans-cycloadipic acid, 1.06g of DMAP, and 22g of tert-butanol into a 100ml reaction bottle, pre-cool in an ice-water bath to 0-5°C, then slowly add 32g of BOC anhydride dropwise under stirring, and react at 30°C 10 hours. The reaction solution was spin-dried, dissolved in 60ml of DCM, and filtered with suction. Then the DCM organic phase was washed twice with 50 ml of 0.5 mol / L dilute hydrochloric acid, washed once with 50 ml of water, and the organic phase was dried. Spin dry to obtain trans-cyclohexanedicarboxylate bis-tert-butyl.

[0043] (2) Hydrolysis reaction:

[0044] Add 12g of tetrahydrofuran to dissolve trans-bis-tert-butyl cyclohexanedicarboxylate, cool to 15°C, and add 2.4g of potassium tert-butoxide. After the addition, the reaction was sealed for 10 hours, and the hydrolysis reaction was completed. The reaction solution was spin-dried, dissolved in 10ml of water, back-extracted twice with 10ml of DCM. ...

Embodiment 2

[0047] Except following conditions, other operation is the same as embodiment 1.

[0048] (1) Esterification: 11 g of trans-cycloadipic acid, 2 g of DMAP, and 40 g of tetrahydrofuran were added at 0°C and kept at 30°C for 5 hours.

[0049] (2) Hydrolysis: 4.1 g of sodium tert-butoxide and 21 g of dichloromethane were dissolved.

[0050] Table 1 is the final yield and purity data of each embodiment two-step reaction.

[0051] Table 1

[0052] final yield purity Example 1 74％ 99.0％ Example 2 71％ 98.7％

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Abstract

The invention discloses a method for synthesizing trans-1, 4-cyclic mono-tert-butyl adipate. The method comprises an esterification reaction 1 and a hydrolysis reaction 2, and a reaction intermediateis trans-1, 4-cyclic di-tert-butyl adipate. The method has the advantages of simple process, short flow, simple operation and high yield, and further enhances the purity of the trans-cyclic mono-tert-butyl adipate.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal materials and relates to a method for synthesizing a liquid crystal intermediate; more specifically, it relates to a method for synthesizing trans-1,4-mono-tert-butyl cyclohexanedioate. Background technique [0002] With the development of technology and the rapid growth of market demand, display technology is also constantly improving. Thin film transistor liquid crystal display (TFT-LCD) is an active matrix display formed by introducing a thin film transistor switch into a twisted nematic liquid crystal display (TN), which eliminates cross-interference, less information, slow writing speed and other shortcomings, greatly improving the Display quality. TFT-LCD is a display device that completely catches up with and surpasses CRT in terms of brightness, contrast, power consumption, lifespan, volume and weight. It has the advantages of excellent performance, good mass production characteri...

Claims

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Application Information

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IPC IPC(8): C07C67/30C07C69/757
CPCC07C67/30C07C67/08C07C2601/14C07C69/757
Inventor 刘欣来源谭玉东靳灿辉
Owner 江苏创拓新材料有限公司
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