1, 3-diphenyl-1-propanol and method for synthesizing 1, 3-diphenyl-1-propanol from nitromethane

A technology of diphenylpropanol and nitromethane, applied in the direction of organic chemical methods, chemical instruments and methods, preparation of hydroxyl compounds, etc., can solve the problems of poor practicability and uneconomical splitting methods, and achieve low cost and simple operation Effect

Active Publication Date: 2018-06-08
HUBEI YUANDA FUCHI PHARMA CHEM
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Problems solved by technology

[0035] Most of the methods listed above will use expensive chemical reagents, which is poor in practicability, and the split method is uneconomical

Method used

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  • 1, 3-diphenyl-1-propanol and method for synthesizing 1, 3-diphenyl-1-propanol from nitromethane
  • 1, 3-diphenyl-1-propanol and method for synthesizing 1, 3-diphenyl-1-propanol from nitromethane

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Embodiment 1

[0070] This embodiment provides a method for synthesizing 1,3-diphenyl-1-propanol from nitromethane, and its specific steps are as follows:

[0071] S11, the preparation of 2-phenylnitroethane, dissolve 6.1g nitromethane (0.1mol), 10.6g benzaldehyde (0.1mol) in 100ml methanol, add 2g sodium hydroxide (0.05mol) under stirring, Stir at room temperature (25°C) until the solution is clear, then add 4g of sodium borohydride (0.11mol), and continue to stir for 2 hours. After the thin plate shows no reactants, acidify with 2N hydrochloric acid, extract with ethyl acetate, and combine the extracts with bicarbonate Wash with sodium aqueous solution and saturated sodium chloride aqueous solution, dry and concentrate to obtain 2-phenylnitroethane.

[0072] S12, the preparation of 3-nitro-1,3-diphenylpropanol, 60mgL-proline derivative (0.25mmol, mole percent 2.5mol%) and 63mg dihydrate cupric chloride (0.25mmol, mole percent 2.5mol%) was added to 40ml tetrahydrofuran, stirred at room tem...

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Abstract

The invention discloses 1, 3-diphenyl-1-propanol and a method for synthesizing the 1, 3-diphenyl-1-propanol from nitromethane, and belongs to the technical field of chemical synthesis. The method forsynthesizing the 1, 3-diphenyl-1-propanol from the nitromethane, provided by the invention, comprises the following steps: performing a reaction on the nitromethane and benzaldehyde in an alkaline environment under the action of sodium borohydride to obtain 2-phenylnitroethane; performing a reaction on the 2-phenylnitroethane and the benzaldehyde under the actions of an L-valine derivative and anadditive to obtain 2-nitro-1, 3-diphenylpropanol; and performing a reaction on the 2-nitro-1, 3-diphenylpropanol under the actions of tributyl tin hydride and azobisisobutyronitrile to remove nitro toobtain the 1, 3-diphenyl-1-propanol. The preparation method is simple in operation and low in cost; and by the preparation method, a product with the required optical purity can be prepared. In addition, the invention further relates to the 1, 3-diphenyl-1-propanol prepared by the preparation method.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, and in particular to a method for synthesizing 1,3-diphenyl-1-propanol from 1,3-diphenyl-1-propanol and nitromethane. Background technique [0002] 1,3-Diphenyl-1-propanol and its derivatives are important chemical intermediates, which are widely used in medicine and agricultural chemicals, and can be used to prepare artificial immunosuppressants, prevent and treat neurodegeneration Diseases, anticoagulation, anti-abnormal proliferation, inhibition of β-secretase, antibacterial, inhibition of HIV-1 protease, etc., so the synthesis of such compounds has been extensively studied, so far the 1,3-di Phenyl-1-propanol preparation methods can be divided into the following categories: [0003] 1. Obtained by reduction of the corresponding ketone: [0004] Synthesis, 2007, 24, 3877-3885; [0005] Monatshefte fur Chemie, 2008, 139(7), 793-798; [0006] Tetrahedron Letters, 2011, 52(22), 282...

Claims

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Application Information

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IPC IPC(8): C07C33/24C07C29/00C07C201/12C07C205/04C07C205/16
CPCC07B2200/07C07C29/00C07C201/12C07C205/04C07C205/16C07C33/24
Inventor 雷大有杨尚金杨长云谢国范
Owner HUBEI YUANDA FUCHI PHARMA CHEM
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