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Preparation method of 1, 4-dihydroxy-phenyl ketone

A technology of phenyl ketone and dihydroxyl, which is applied in the field of preparation of 1,4-dihydroxy-phenyl ketone, can solve the problems of only 60% conversion rate, high operation requirements, unreacted by-product resorcinol and the like , to achieve the effect of effective recycling and utilization, simple process and easy recycling

Inactive Publication Date: 2015-02-04
SUZHOU JONATHAN NEW MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the 1920s, documents such as J.Am.Chem.Soc., 1921,43(2), 348-360, U.S. US1649672, and Canadian Patent CA272351 have reported the use of anhydrous zinc chloride as a catalyst and solvent-free The method for preparing 1,4-dihydroxy-phenyl ketone under normal circumstances, but it is easy to cause a large amount of by-products or a large amount of unreacted raw material resorcinol
In 1926, the method reported by J.Am.Chem.Soc., 48,2206-12 used anhydrous zinc chloride as a catalyst and fatty acid ethyl ester as an acylating agent to prepare 1,4-dihydroxy-phenyl ketone, but A large amount of raw materials in this method are not converted, and the conversion rate is only 60%.
[0007] In addition, there are also reports (Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), (12), 2894-900) using fatty nitriles as acylating reagents in trifluoromethanesulfonic acid The method for preparing alkyl ketone under catalysis, its raw material fatty nitrile and catalyst trifluoromethanesulfonic acid are relatively expensive, and it is not an economical production method
[0008] It can be seen that the current methods for producing 1,4-dihydroxy-phenyl ketone are not very ideal, or there are many by-products, or the conversion rate of raw materials is low, or the reaction conditions are harsh, the operation requirements are high, the yield is low, and the cost is high

Method used

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  • Preparation method of 1, 4-dihydroxy-phenyl ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 9.9g of n-butyric acid, 21mL of toluene, and 10g of anhydrous zinc chloride into a 50mL flask, immerse in a preheated 100°C oil bath, stir to a constant temperature, add 6.05g of resorcinol, and stir for 30min. Raise the temperature to 110°C, continue the reaction for 5 hours, cool to 0-5°C, separate the lower layer of zinc chloride (with n-butyric acid, a small amount of resorcinol and products), and wash the toluene layer with 6M hydrochloric acid 1-2 times, 10 % sodium hydroxide (20mL*5) was fully extracted, the extracted water phase was adjusted to a pH value of about 3.0 with concentrated hydrochloric acid, a large amount of solids were precipitated, cooled to 5-10°C, suction filtered, washed with water, recrystallized with 37.5% ethanol aqueous solution, 7.8 g of yellow needle-like crystals were obtained, and the product yield was 79% (calculated by resorcinol).

Embodiment 2

[0030] Add 10.45g of n-propionic acid, 32mL of cyclohexane, 6.05g of resorcinol, and 10g of anhydrous zinc chloride into a 100mL flask, immerse in a preheated oil bath, reflux with water for 6 hours, and cool to 0 ~5°C, separate the lower layer of zinc chloride (with n-propionic acid, a small amount of resorcinol and products), wash the organic layer with 6M hydrochloric acid for 1 to 2 times, and fully extract with 10% sodium hydroxide (20mL*5) Afterwards, extract the aqueous phase and use concentrated hydrochloric acid to adjust the pH value to about 3.0, a large amount of solids are precipitated, cooled to 5-10 ° C, filtered with suction, washed with water, and recrystallized with 35% ethanol aqueous solution to obtain 7.1 g of yellow needle-shaped crystals. The product yield is 77%.

Embodiment 3

[0032] Add 9.74g of n-hexanoic acid, 35mL of xylene, and 10g of anhydrous zinc chloride into a 100mL flask, immerse in a preheated 100°C oil bath, stir to a constant temperature, add 6.05g of resorcinol, and stir for 30min. Raise the temperature to 120°C, continue the reaction for 5.5 hours, cool to 0-5°C, separate the lower layer of zinc chloride (containing n-hexanoic acid, a small amount of resorcinol and products), and wash the xylene layer with 6M hydrochloric acid for 1-2 times. Fully extract with 10% sodium hydroxide (20mL*5), adjust the pH value of the extracted water phase to about 3 with concentrated hydrochloric acid, precipitate a large amount of solid, cool to 5-10°C, filter with suction, wash with water, recrystallize with 39% ethanol aqueous solution, 8.9 g of yellow needle-like crystals were obtained, and the product yield was 76%.

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PUM

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Abstract

The invention provides a preparation method of 1, 4-dihydroxy-phenyl ketone. In an organic medium, anhydrous zinc chloride is taken as a catalyst, and resorcinol and saturated fatty acid are subjected to acylation reaction at the temperature of 80-140 DEG C to prepare a target product, namely 1, 4-dihydroxy-phenyl ketone. The preparation method of 1, 4-dihydroxy-phenyl ketone provided by the invention is simple in process flow, few in byproducts and high in yield, the catalyst is easy to recycle, and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular, the invention relates to a preparation method of 1,4-dihydroxy-phenyl ketone. Background technique [0002] 1,4-dihydroxy-phenyl ketone is a kind of important pharmaceutical and daily chemical intermediates, and its use is very wide. Its structure is shown in the following formula, where R is CnH2n+1, n: 1,2, 3……. 1,4-dihydroxy-phenyl ketone can be used as an intermediate for the preparation of cosmetic preservatives and cosmetic active substances, and its downstream products can be used as whitening agents, which have anti-aging, whitening, antibacterial and other effects. [0003] [0004] At present, there are few literatures on the synthesis methods of 1,4-dihydroxy-phenyl ketone, and even fewer methods suitable for production. [0005] The synthesis of 1,4-dihydroxy-phenyl ketone is generally obtained by resorcinol through the Fox acylation reaction (F-C reactio...

Claims

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Application Information

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IPC IPC(8): C07C49/825C07C45/46
CPCY02P20/584C07C45/46C07C45/80C07C45/81C07C49/825
Inventor 李卓才李苏杨
Owner SUZHOU JONATHAN NEW MATERIALS TECH
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