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Photocatalytic oxidation synthesis method of diphenylmethanol ester

A photocatalytic oxidation and diphenyl alcohol technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as complex preparation of diphenyl alcohol, and achieve energy saving effect

Active Publication Date: 2019-02-22
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation of diphenylmethanol itself is relatively complicated, so the direct one-step reaction to prepare diphenylmethanol esters has attracted people's attention recently.

Method used

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  • Photocatalytic oxidation synthesis method of diphenylmethanol ester
  • Photocatalytic oxidation synthesis method of diphenylmethanol ester
  • Photocatalytic oxidation synthesis method of diphenylmethanol ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the preparation of benzhydrin acetate (formula (1-1))

[0023] Add 1mmol of diphenylmethane, 4mmol of acetic acid, 0.2mmol of DDQ and 200mg of 3A molecular sieve into a sealed 25mL tube equipped with a magnetic stirring bar, replace the air in the tube with oxygen, seal the bottle mouth with a rubber stopper, and insert an oxygen balloon , then inject 0.2mmol of TBN and 5mL of 1,2-dichloroethane into the sealed tube, react at room temperature for 24h under the irradiation of 18W blue LED lamp, evaporate the solvent under reduced pressure, and then conduct column chromatography separation, A mixture of ethyl acetate / petroleum ether with a volume ratio of 1:100 was used as the eluent to collect the eluate containing the target compound, and the solvent was evaporated to obtain the product diphenylmethanol acetate with an isolated yield of 82%.

Embodiment 2

[0024] Embodiment 2: the preparation of benzhydrin acetate (formula (1-1))

[0025] The reaction steps are the same as in Example 1, except that the consumption of DDQ is changed to 0.15mmol, the consumption of TBN is changed to 0.25mmol, the consumption of acetic acid is changed to 5mmol, and the separation yield of benzhydrin acetate is 80%.

Embodiment 3

[0026] Embodiment 3: the preparation of benzhydrin acetate (formula (1-1))

[0027] The reaction steps are the same as in Example 1, except that the consumption of DDQ is changed to 0.25mmol, the consumption of TBN is changed to 0.15mmol, the consumption of acetic acid is changed to 3mmol, and the separation yield of benzhydrin acetate is 78%.

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Abstract

The invention discloses a photocatalytic oxidation synthesis method of diphenylmethanol ester. The method is characterized in that diphenylmethanol and carboxylic acid are used as reaction substrates,2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert-butyl nitrite (TBN) are used as a catalyst, and oxygen is used as an oxidant, in the presence of 3A or 4A molecular sieves, the reaction substrates react in the 1,2-dichloroethane solvent under conditions of room temperature, normal pressure and blue light irradiation, and after the reaction ends, a diphenylmethanol ester compound is obtained by separation treatment. According to the invention, by replacing the traditional heating reaction with light reaction, the energy is saved; and the reaction is environmentally friendly by using oxygen as the oxidant.

Description

technical field [0001] The invention relates to a photocatalytic oxidation synthesis method of benzhydryl alcohol ester. Background technique [0002] Benzhydryl alcohol esters are an important class of compounds that can be used as raw materials for a variety of reactions to synthesize a variety of products. In view of the important role of benzhydryl alcohol esters, the exploration of their synthetic methods is also in progress. Traditionally, diphenylmethanol can be used as a raw material to synthesize diphenylmethanol esters through catalyzed esterification. However, the preparation of diphenylmethanol itself is relatively complicated, so the direct one-step reaction to prepare diphenylmethanol esters from relatively cheap and easily available diphenylmethane has attracted people's attention recently. Literature (ChemSusChem 2012,5:2143) reported stoichiometric 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as an oxidant, in dichloroethane solvent, At 100 degrees, di...

Claims

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Application Information

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IPC IPC(8): C07C69/157C07C69/24C07C69/78C07C67/08C07C67/56
CPCC07C67/08C07C67/56C07C69/157C07C69/24C07C69/78
Inventor 沈振陆赵雅静潘得成李美超
Owner ZHEJIANG UNIV OF TECH
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