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Method for preparing 4-n-butyl resorcinol by one-pot method

A technology of n-butyl resorcinol and resorcinol, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as environmental pollution and production safety reduction, and achieve atomic utilization High efficiency, easy operation and high yield

Active Publication Date: 2020-02-18
CHONGQING DONGHUAN SCI & TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the method of reducing carbonyl to methylene by Wolff-Kishner-Huang Minglong reaction or Clemmensen reduction reaction uses a large amount of hydrazine or zinc amalgam, which reduces the production safety and pollutes the environment, and uses highly toxic mercury reagents , purchases are restricted while zooming in

Method used

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  • Method for preparing 4-n-butyl resorcinol by one-pot method
  • Method for preparing 4-n-butyl resorcinol by one-pot method
  • Method for preparing 4-n-butyl resorcinol by one-pot method

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Experimental program
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Effect test

Embodiment 1

[0020]

[0021] Under the protection of nitrogen, put 110g (1mol) of resorcinol and 350g of toluene into the reaction bottle to mix and dissolve, then cool down to 10°C, add 98g (1.02mol) of sodium n-butoxide in batches, and control the temperature at 10-15°C, TLC (EA developer) After detecting that there are almost no remaining raw materials, add n-butanol (2.2mol), 27.2g (0.2mol) of zinc chloride and 1.1g of calcium chloride, raise the temperature to 40-45°C for 1 hour, and then raise the temperature to 102 ℃ to carry out reflux water separation, after 6 hours of water separation, sampling and quenching GC to detect resorcinol 1 HNMR (400MHz, CDCl 3 ):0.96(t,3H),1.35-1.62(m,4H),2.55(m,2H),6.15-6.24(m,2H),6.75(s,1H),8.46(s,1H),12.83( s, 1H).

Embodiment 2

[0023]

[0024] Under the protection of nitrogen, put 110g (1mol) of resorcinol and 350g of xylene into the reaction bottle to mix and dissolve, then cool down to 10°C, add 113.3g (1.01mol) of potassium n-butoxide in batches, and control the temperature at 10-15°C , TLC (EA developer) detects that there is almost no remaining raw material, add n-butanol (2.2mol), zinc chloride 27.2g (0.2mol) and concentrated sulfuric acid 2.2g, heat up to 40-45°C for 1 hour, then heat up to Reflux at 112°C for water separation. After 4 hours of water separation, sample and quench GC to detect resorcinol 1 HNMR (400MHz, CDCl 3 ):0.96(t,3H),1.35-1.62(m,4H),2.55(m,2H),6.15-6.24(m,2H),6.75(s,1H),8.46(s,1H),12.83( s, 1H).

Embodiment 3

[0026]

[0027] Under the protection of nitrogen, put 110g (1mol) of resorcinol and 350g of m-chlorobenzene into the reaction bottle to mix and dissolve, then cool down to 10°C, add 81.7g (1.02mol) of lithium n-butoxide in batches, and control the temperature for 10-15 ℃, after TLC (EA developer) detects that almost no raw materials are left, add n-butanol (2.5mol), zinc chloride 272g (0.2mol) and anhydrous copper sulfate 1.5g, raise the temperature to 40-45℃ for 1 hour, and then Raise the temperature to 113°C for reflux and water separation. After 4 hours of water separation, take a sample and quench the GC to detect resorcinol <1%, cool down to room temperature, filter out the solid catalyst through diatomaceous earth, and add dilute sulfuric acid to adjust the pH=1 -2. Concentrate the organic phase to stagnant liquid, add water to replace, then add 660g water, 2.2g sodium thiosulfate and 5.5g activated carbon, heat up to reflux for 1 hour, heat filter to obtain a light ye...

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Abstract

The invention discloses a method for preparing 4-n-butyl resorcinol by a one-pot method, and belongs to the field of cosmetic intermediate synthesis. The method comprises the following steps of: reacting resorcinol serving as a raw material with an alkali in n-butyl alcohol to form monophenol salt, reacting the monophenol salt with a Lewis acid by a dehydration one-pot method, performing acidolysis to obtain a crude product, and recrystallizing to obtain the 4-n-butyl resorcinol. The method is simple and convenient to operate, mild in condition, low in cost and high in yield, the purity of theobtained product can reach 99.0% or above, and the method has a potential amplification prospect.

Description

technical field [0001] The invention relates to a method for preparing 4-n-butylresorcinol by a one-pot method, and belongs to the technical field of chemical intermediate synthesis. Background technique [0002] 4-n-butyl resorcinol, alias 4-butyl resorcinol, English name 4-butyl-resorcinol, molecular formula is C 10 h 14 o 2 , the molecular weight is 166.22, and the CAS is 18979-61-8. It is often used as a whitening additive for skin care products. It can be used to synthesize FXR agonist intermediates and treat cholestasis, high cholesterol, heart disease and other diseases. It is mainly used in spices, medicines, and dyes. and other fields. [0003] At present, the synthesis method of this product literature is mainly resorcinol and n-butyric acid in AlCl 3 Under catalysis, the Fuckers acylation reaction was carried out, and then the carbonyl group was reduced to methylene by Wolff-Kishner-Huang Minglong or Clemmensen reduction reaction to obtain 4-butylresorcinol wi...

Claims

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Application Information

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IPC IPC(8): C07C37/11C07C39/08
CPCC07C37/11C07C37/66C07C39/08C07C39/235
Inventor 张克伦张太军
Owner CHONGQING DONGHUAN SCI & TECH DEV
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