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Preparation method of 1-phenyl-2-nitroethanol and derivatives thereof

A technology of nitroethanol and derivatives, which is applied in the field of preparation of 1-phenyl-2-nitroethanol and its derivatives, can solve the problems that solid phase catalysis has not been studied, and has not been used in Henry reaction. Strong effect, high utilization rate, less environmental pollution

Active Publication Date: 2020-12-25
NANJING UNIV OF INFORMATION SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, although there are many kinds of ion exchange resins with catalytic function, they are not used in Henry reaction, and the solid phase catalysis of this reaction has not been studied.

Method used

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  • Preparation method of 1-phenyl-2-nitroethanol and derivatives thereof
  • Preparation method of 1-phenyl-2-nitroethanol and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017]Activation of strong basic ion exchange resin

[0018]Weigh 30g of ion-exchange resin and load it into the chromatography column, which accounts for about 2 / 3 of the height of the chromatography column. Add deionized water to soak. The surface of the water is submerged in the resin. Do not leave bubbles in the middle. Wash 3 times. Turn on the knob, add 5% HCl solution while draining water, until the outflow liquid is acidic, close the knob and soak for 1 hour, the ion exchange resin is bright yellow. Discharge the acid liquid and wash with water 3 times until the outflow liquid is neutral. Add 5% NaOH solution until the outflowing liquid is alkaline. After soaking for 1 hour, the ion exchange resin turns orange. Wash 3 times to neutral. Repeat pickling, washing, alkali washing, and washing once. Finally, a catalytically active ion exchange resin is obtained.

Embodiment 2

[0020]Preparation of 2-(2,4-dichloro)phenyl-1-nitroethanol

[0021]Add 5.4mL (0.1mol) nitromethane, 1.70g (0.01mol) 2,4-dichlorobenzaldehyde, 15mL tert-butanol to a 100mL flask, stir at room temperature to mix well, and add 3.0g of the above activated strong base Ion exchange resin, continue to stir and react for 3h. TLC monitoring showed a sufficient reaction. Suction and filter out the resin. After the filtrate was rotary evaporated, the solvent and unreacted nitromethane were distilled out to obtain a yellow oil. After standing at room temperature for 4 hours, the product was crystallized, recrystallized with petroleum ether, and dried to obtain 1.87 g of a yellowish powdery solid with a yield of 82 %, mp78-80°C. In addition, the post-treatment method can also be used to directly pour the reaction liquid into ice water, collect the lower oil droplets, and place them in the air to crystallize.

[0022]The characterization parameters of the prepared product are as follows:

[0023]1H NMR(50...

Embodiment 3

[0026]Preparation of 2-phenyl-1-nitroethanol

[0027]Prepared by the reaction of benzaldehyde and nitromethane, raw materials: 0.1 mol of nitromethane, 0.01 mol of benzaldehyde, solvent: 15 mL of tert-butanol, catalyst: 3.0 g of activated strong basic ion exchange resin, the synthesis method is the same as in Example 2. The product is a yellow-brown oil, does not crystallize at room temperature, and the yield is 70%.

[0028]The characterization parameters of the prepared product are as follows:

[0029]1H NMR(500MHz, CDCl3)δ7.41–7.35(m,5H,Ar-H), 5.45(dd,J=10,3Hz,1H,CH-O), 4.60(dd,J=13.5Hz,10Hz,1H,-CH2-),4.51(dd,J=13.5Hz,3Hz,1H,-CH2-), 2.73 (bs, 1H, -OH).

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Abstract

The invention discloses a preparation method of 1-phenyl-2-nitroethanol and a derivate thereof. The preparation method is characterized in that benzaldehyde or a derivate thereof and nitromethane aretreated as raw materials; tertiary butanol is treated as a solvent; strong alkality type chloride 717 anion exchange resin is treated as a catalyst; and on the basis, Henry reaction is carried out toprepare the 1-phenyl-2-nitroethanol and the derivate. With the adoption of the method for preparing phenyl nitroalcohol, the catalyst effect is high; the synthesizing reaction transformation rate is high; the yield is 60-80%; the catalyst in a product can be simply removed by filtering in post-treatment, so that the post-treatment operation is simplified.

Description

Technical field[0001]The present invention designs a method for preparing 1-Phenyl-2-nitroethanol and its derivatives (1-Phenyl-2-nitroethanol and its derivatives) by catalyzing the Henry reaction with a strong basic ion exchange resin.Background technique[0002]β-amino alcohol drugs are common natural products and marketed drugs. The compound with aryl β-aminoethanol is an adrenergic receptor agonist drug. For example, salmeterol and salbutamol have 1-phenyl-2 -Aminoethanol structure, used to treat cardiovascular diseases and respiratory diseases, and β-amino alcohol can be obtained by the reduction of β-nitro alcohol, such as Zhou Wei et al. (Zhou Wei, Liu Juntao, Lu Yixiang, Jia Xian, Li Xingshu. Chinese Journal of Medicinal Chemistry, 2009, Vol.19, No 2, 123-126) Salmeterol has been prepared by this method.[0003][0004]The preparation of β-nitroalcohol is mainly completed by Henry reaction. The catalysts currently used in Henry reaction are mainly divided into inorganic bases, org...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C201/12C07C205/26C07C205/16C07C205/19B01J31/08
CPCB01J31/08C07C201/12C07C205/26C07C205/16C07C205/19
Inventor 焦岩吴立康张明道章翔宇
Owner NANJING UNIV OF INFORMATION SCI & TECH
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