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Preparation method for 4-butylresorcinol

A technology of butylresorcinol and butyrylresorcinol, which is applied in the field of preparation of 4-butylresorcinol, can solve the problem of low conversion rate of raw materials or product yield, many by-products, high reaction conditions, etc. problem, achieve the effect of shortening the reaction time, increasing the reaction yield and reducing the production cost

Inactive Publication Date: 2013-06-19
NANJING HUASHI NEW MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] Treat B. Johnson et al. (J. Am. Chem. Soc ., 1921, 43 (2), 348-360) and US1649672, CA272351 used anhydrous zinc chloride as a catalyst to prepare resorcinol alkyl ketone in the synthesis of 4-butylresorcinol, but there were a lot of by-products Or a large amount of unreacted raw material resorcinol
[0020] There are also literature reports on the preparation of resorcinol alkyl ketones using anhydrous zinc chloride as a catalyst and fatty acid ethyl ester as an acylating agent (J. Am. Chem. Soc., 48, 2206-12, 1926), The conversion rate is only 60%; and the method of preparing resorcinol alkyl ketones from fatty acid chlorides and resorcinol in the presence of aluminum trichloride (Gazzetta Chimica Italiana, 114(7-8), 359-61, 1984) , the method is relatively high for reaction conditions, must be carried out under anhydrous conditions, and the yield is low, only 60%
[0021] In the prior art, in the preparation of 4-butyl resorcinol, there are also difficulties in the preparation of intermediate resorcinol alkyl ketones. The problem is that there are many by-products, low raw material conversion rate or product yield, or operating requirements High, the cost is also high

Method used

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  • Preparation method for 4-butylresorcinol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049]Under nitrogen protection, put 15g of potassium hydroxide and 22mL of diethylene glycol into the flask, immerse in a preheated 100°C oil bath, stir until the solid dissolves, add 8.0g of 4-butyryl resorcinol, Continue to stir until it is completely dissolved, add hydrazine hydrate dropwise, and the solution turns dark green. After the dropwise addition, heat to reflux for 2 hours, distill out hydrazine hydrate until the internal temperature reaches 190°C, and continue to reflux the residue for 3-4 hours. TLC detects that there is no raw material. Cool the reaction solution, add concentrated hydrochloric acid dropwise to pH 3.0, add ice water and ethyl acetate for extraction, wash the organic phase with a saturated solution of sodium bicarbonate, wash with saline, dry over anhydrous sodium sulfate, and concentrate to obtain a brown-red oily liquid, which is washed by 6.2 g of colorless solid recrystallized from benzene.

[0050]

Embodiment 2

[0052] Under nitrogen protection, put 17g of sodium hydroxide and 22mL of diethylene glycol into the flask, immerse in a preheated 100°C oil bath, stir until the solid dissolves, add 8.0g of 4-butyryl resorcinol, Continue to stir until it is completely dissolved, add hydrazine hydrate dropwise, and the solution turns dark green. After the dropwise addition, heat to reflux for 2 hours, distill out hydrazine hydrate until the internal temperature reaches 190°C, and continue to reflux the residue for 3-4 hours. TLC detects that there is no raw material. Cool the reaction solution, add concentrated hydrochloric acid dropwise to pH 3.0, add ice water and ethyl acetate for extraction, wash the organic phase with a saturated solution of sodium bicarbonate, wash with saline, dry over anhydrous sodium sulfate, and concentrate to obtain a brown-red oily liquid, which is washed by 5.9 g of colorless solid recrystallized from benzene.

[0053]

Embodiment 3

[0055] Under the protection of nitrogen, put 15g of potassium hydroxide and 22mL of triethylene glycol into the flask, immerse in a preheated 100°C oil bath, stir until the solid dissolves, add 8.0g of 4-butyryl resorcinol, continue Stir until completely dissolved, add hydrazine hydrate dropwise, the solution turns dark green, after the dropwise addition, heat to reflux for 2 hours, distill out hydrazine hydrate until the internal temperature reaches 200 0 ℃, the residue continued to reflux for 3-4 hours, TLC detected no raw materials, cooled the reaction solution, added concentrated hydrochloric acid dropwise to pH 3.0, added ice water and ethyl acetate for extraction, and washed the organic phase with saturated sodium bicarbonate solution and brine. Dry over anhydrous sodium sulfate and concentrate to obtain a brownish-red oily liquid, and 6.1 g of a colorless solid recrystallized from benzene.

[0056]

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Abstract

The present invention discloses a preparation method for 4-butylresorcinol, wherein a Huang Minlon reduction method is used to reduce 4-butyrylresorcinol to give the 4-butyl resorcinol. The method concretely includes the following steps: 1) heating to solve a certain amount of an organic solvent, 4-butylresorcinol and an alkali, adding dropwise excess hydrazine hydrate, and refluxing for 1-3h under heating; 2) distilling off the excess hydrazine hydrate until the reaction solution is heated to 170-220 DEG C; 3) maintaining the reaction temperature at 170-220 DEG C, and refluxing for 1-4h under heating, until the reaction is complete; and 4) cooling, neutralizing, and extracting the reaction solution, and washing, concentrating after drying and recrystallizing an organic phase to give the 4-butylresorcinol. Because the Huang Minlon reduction method is adopted, the method of the present invention has characteristics of being simple in the process, high in the conversion rate, and environment-friendly; and combined with an improved preparation method for intermediate 4-butyrylresorcinol, the production cost can be further reduced.

Description

technical field [0001] The invention relates to a preparation method of 4-butylresorcinol. Background technique [0002] Hyperpigmentation often occurs in menopausal women. The accumulation of melanin in the skin causes hyperpigmentation, including melasma, freckles and age spots. Melanocytes are specialized cells in the skin that produce melanin. Those with darker skin do so because their melanocytes can store more melanin. The main function of melanocytes is to form melanin. The normal and healthy skin color of the human body is the result of the balance of melanin synthesis and metabolism. [0003] 4-Butylresorcinol can be used in cosmetics as a whitening agent, antioxidant and preservative. Its main features are: 1) Inhibit melanin, chloasma and freckles. 2) Anti-UV. 3) Penetrates quickly and quickly reaches the deep layer of the skin. 4) High safety and low allergenicity. Its structure is shown in the following formula. [0004] [0005] 4-Butylresorcinol can ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/08C07C37/00
Inventor 史鲁秋苏桂珍薛虹宇
Owner NANJING HUASHI NEW MATERIAL
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