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A method for synthesizing 3,9-di(4-carboxyphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane

A technology of tetraoxaspiro and carboxyphenyl, applied in the field of chemistry, can solve the problems of expensive catalyst, difficult removal, low yield and the like, and achieves the effects of long reaction time, low yield and improved yield

Active Publication Date: 2020-06-02
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] There are solvent N in the above-mentioned method, and the boiling point of N.dimethylformamide is high, it is difficult to remove, the catalyst is expensive, the reaction time is long (the reactant has acidity), and the defects such as low yield

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] A method for rapidly synthesizing 3,9-bis(4-carboxyphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, comprising the following steps:

[0021] 1) fully grinding pentaerythritol and methyl p-formylbenzoate, the mol ratio of pentaerythritol and methyl p-formylbenzoate is 1:2.2;

[0022] 2) After temperature-controlled melting, add 1% reactant mass p-toluenesulfonic acid catalyst to instantly synthesize 3,9-bis(4-formylmethylphenyl)-2,4,8,10-tetraoxaspiro [5.5] Undecane;

[0023] 3) The above crude product was soaked in ethanol and purified by suction filtration, with a yield of 85%;

[0024] 4) Under reflux conditions, dissolve 3,9-bis(4-carboxymethylphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane in concentrated NaOH solution until clear;

[0025] 5) The reaction solution was cooled and left to stand, and the solid was precipitated, and filtered with suction to obtain the sodium salt of 3,9-bis(4-carboxyphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane , 3,9-bis(4-carboxyphenyl)-2,4,...

Embodiment 2

[0028] A method for rapidly synthesizing 3,9-bis(4-carboxyphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, comprising the following steps:

[0029] 1) fully grinding pentaerythritol and methyl p-formylbenzoate, the mol ratio of pentaerythritol and methyl p-formylbenzoate is 1:2.3;

[0030] 2) After temperature-controlled melting, add 1% reactant mass p-toluenesulfonic acid catalyst to instantly synthesize 3,9-bis(4-formylmethylphenyl)-2,4,8,10-tetraoxaspiro [5.5] Undecane;

[0031] 3) The above crude product was soaked in ethanol and purified by suction filtration, with a yield of 80%;

[0032] 4) Under reflux conditions, dissolve 3,9-bis(4-carboxymethylphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane in concentrated NaOH solution until clear;

[0033] 5) The reaction solution was cooled and left to stand, and the solid was precipitated, and filtered with suction to obtain the sodium salt of 3,9-bis(4-carboxyphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane , 3,9-bis(4-carboxyphenyl)-2,4,...

Embodiment 3

[0036] A method for rapidly synthesizing 3,9-bis(4-carboxyphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, comprising the following steps:

[0037] 1) Fully grinding pentaerythritol and methyl p-formylbenzoate, the mol ratio of pentaerythritol and methyl p-formylbenzoate is 1:2.5;

[0038] 2) After temperature-controlled melting, add 1% reactant mass p-toluenesulfonic acid catalyst to instantly synthesize 3,9-bis(4-formylmethylphenyl)-2,4,8,10-tetraoxaspiro [5.5] Undecane;

[0039] 3) The above crude product was soaked in ethanol and purified by suction filtration, with a yield of 76%;

[0040] 4) Under reflux conditions, dissolve 3,9-bis(4-carboxymethylphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane in concentrated NaOH solution until clear;

[0041] 5) The reaction solution was cooled and left to stand, and the solid was precipitated, and filtered with suction to obtain the sodium salt of 3,9-bis(4-carboxyphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane , 3,9-bis(4-carboxyphenyl)-2,4,...

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Abstract

The invention discloses a method for rapidly synthesizing 3,9-di(4-carboxylphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane. The intermediate 3,9-di(4-carboxylphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane is synthesized through a solvent-free technology, so the problems of high boiling point and difficult removal of a solvent N,N-dimethyl formamide are solved; a catalyst adopts a routine protonic acid, such as p-toluenesulfonic acid and hydrochloric acid, so the catalyst has low price and solves the problem of high price of a ZrCl4 catalyst; a non-acidic reactant methyl p-formylbenzoate is adopted to substitute 4-formylbenzoic acid, so a reaction is instantly finished, and the problem of long reaction time is solved; and synthesis in the invention is carried out in a two-step manner, the yield of the first step is greater than 80%, the alkaline hydrolysis and acid precipitation yield of the second step is greater than 95%, and the comprehensive yield is greater than 76%, so the yield is near 21% higher than those in literature methods, and the problem of low yield is solved.

Description

technical field [0001] The invention specifically relates to a method for rapidly synthesizing 3,9-bis(4-carboxyphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, which belongs to the technical field of chemistry. Background technique [0002] 3,9-bis(4-carboxyphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane is an important organic synthesis intermediate and raw material for many organic synthesis, especially suitable for For the development of coordination compounds, its carboxyl group can coordinate with different metal ions to form coordination compounds with different structures, which is of great significance for the development of functional coordination compounds. At the same time, the C atom of the spiro ring has chirality, which provides the possibility for the development of chiral drugs and chiral complexes. [0003] At present, there are few literature reports on 3,9-bis(4-carboxyphenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane. The research group of Professor Wei Rongbao from ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10
CPCC07D493/10
Inventor 郑晓凤李文强
Owner QUFU NORMAL UNIV
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