2, 6-di-tert-butyl-4-(2-methoxyphenylmethylene)-2, 5-cyclohexadiene-1-one and preparation method thereof

Abstract

The invention discloses 2, 6-di-tert-butyl-4-(2-methoxyphenylmethylene)-2, 5-cyclohexadiene-1-one. A preparation method of 2, 6-di-tert-butyl-4-(2-methoxyphenylmethylene)-2, 5-cyclohexadiene-1-one comprises the following steps: 1) preparing a Mannich base: heating 2, 6-di-tert-butylphenol and ortho-anisaldehyde to reflux temperature of 100-160 DEG C, then performing heat preservation and dropwise adding secondary amine; and further performing reflux reaction on 2, 6-di-tert-butylphenol and ortho-anisaldehyde under the catalytic action of secondary amine in solvent-free conditions; 2) removing secondary amine in the Mannich base: performing reduced pressure distillation on a reaction solution obtained in the step 1) to remove secondary amine in the Mannich base so as to obtain a crude product; and 3) recrystallizing the crude product: performing recrystallization on the crude product obtained in the step 2) by adopting a hot melting and cold separation method to obtain 2, 6-di-tert-butyl-4-(2-methoxyphenylmethylene)-2, 5-cyclohexadiene-1-one.

Description

technical field [0001] The present invention relates to a kind of synthetic method of organic compound, especially 2,6-di-tert-butyl-4-(2-methoxybenzylidene)-2,5-cyclohexadien-1-one (QM -ph-o-OMe) preparation method. Background technique [0002] 2,6-Di-tert-butyl-4-(2-methoxybenzylidene)-2,5-cyclohexadien-1-one (QM-ph-o-OMe), whose molecular formula is C 22 h 28 o 2 , whose chemical formula is shown in formula S-1; it is a p-methylene quinone compound. [0003] [0004] At present, there is no literature report about QM-ph-o-OMe and its synthesis method. [0005] By consulting the literature, we found that the preparation methods of its analogue 2,6-di-tert-butyl-4-benzylidene-2,5-cyclohexadien-1-one (QM-ph) mainly include the following : [0006] 1), methylene oxidation method: Mueller E. et al. reported a method of using 2,6-di-tert-butylphenol and benzyl alcohol as raw materials, first adding dehydration and then oxidation to prepare QM-ph, such as formula S -2...

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Problems solved by technology

[0012] The synthesis of QM-ph by methylene oxidation requires the use of a highly toxic solvent, benzene, and an oxidant, potassium ferricyanide, which causes great environmental pollution.

Synthesis of QM-ph by phenyllithium method or Grignard reagent method, the raw materials are phenyllithium and 3,5-di-tert-butyl-4-hydroxybenzaldehyde, the price is more expensive; the reaction needs to be carried out in anhydrous or anhydrous and oxygen-free environment It is carried out under high conditions and has high requirem

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