Preparation method of alpha-naphthylacetic acid

A technology of naphthalene acetic acid and naphthalene ethyl ketone ester, which is applied in the direction of carboxylate preparation, carboxylate preparation, carboxylate preparation, etc., can solve the problems of high environmental protection costs, expensive α-naphthylacetone, etc., and achieve production costs Low, easy to purify, high yield effect

Pending Publication Date: 2020-08-07
ZHEJIANG SCI-TECH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] However, its raw material α-naphthyl ethyl ketone is relatively expensive; highly toxic and extremely smelly hydrogen sulfide gas and a l

Method used

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  • Preparation method of alpha-naphthylacetic acid
  • Preparation method of alpha-naphthylacetic acid
  • Preparation method of alpha-naphthylacetic acid

Examples

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Example Embodiment

[0036] Example 1

[0037] In the reaction flask, add 120 mL (1.5 mol) 1,2-dichloroethane, 14.8 g (0.111 mol) anhydrous aluminum trichloride and 12.8 g (0.1 mol) naphthalene; after stirring, heat to 45 ℃ , Add 12.3 mL (0.115 mol) of oxalyl chloride monoethyl ester; react for 4 hours, after the reaction is complete, pour the reaction mixture into 100 mL of cold water, stir well and let stand to separate the organic layer; the organic layer is subjected to 30 mL 5% hydrochloric acid After acid washing, water washing, and drying with anhydrous sodium sulfate, it was concentrated to obtain an oily substance (product 1); product 1 was directly used in the next reaction without purification.

[0038] Add the above product 1 to the reaction flask, add 110 mL (1.98 mol) ethylene glycol and 12 mL (0.32 mol) hydrazine hydrate (85%); slowly increase the temperature to 130 ℃ with stirring, and react for 2 hours; then cool the reaction solution to Below 80 ℃, add 26.9 g (0.48 mol) potassium hyd...

Example Embodiment

[0039] Example 2

[0040] In the reaction flask, add 120 mL (1.24 mol) carbon tetrachloride, 20.4 g (0.15 mol) anhydrous zinc chloride and 12.8 g (0.1 mol) naphthalene; after stirring, heat to 55 ℃, add 11.0 mL ( 0.12 mol) monomethyl oxalyl chloride; react for 4 hours. After the reaction, pour the reaction mixture into 100 mL of cold water, stir well and let stand, and separate into several layers; the organic layer is acid-washed with 30 mL 5% hydrochloric acid and washed with water. After drying with aqueous sodium sulfate, it was concentrated to obtain an oil (product 1); product 1 was directly used in the next reaction without purification.

[0041] Add the above product 1 to the reaction flask, add 110 mL (1.36 mol) 1,2-propanediol and 6.5 mL (0.21 mol) anhydrous hydrazine; slowly heat up to 130 ℃ with stirring, and react for 2 hours; then cool the reaction solution to 80 Below ℃, add 12g (0.3 mol) sodium hydroxide, then the reaction mixture is heated to 180 ℃ for 4 hours whi...

Example Embodiment

[0042] Example 3

[0043] In the reaction flask, add 95 mL (1.48 mol) dichloromethane, 35 g (0.134 mol) anhydrous tin chloride and 12.8 g (0.1 mol) naphthalene; after stirring, heat to 50 ℃, add 14.5 mL (0.13 mol) mol) Ethyl oxalyl chloride; react for 4.5 hours. After the reaction, pour the reaction mixture into 100 mL of cold water, stir well and let stand, and separate into several layers; the organic layer is acid-washed with 30 mL 5% hydrochloric acid and washed with water. After drying with aqueous sodium sulfate, it was concentrated to obtain an oil (product 1); product 1 was directly used in the next reaction without purification.

[0044] Add the above product 1 to the reaction flask, add 135 mL (1.5 mol) 1,4-butanediol and 18 mL (0.48 mol) hydrazine hydrate (85%); slowly heat up to 140 ℃ with stirring, and react for 2 hours; The reaction solution was cooled to below 80 ℃, and 26.9 g (0.48 mol) potassium hydroxide was added. Then the reaction mixture was heated to 190 ℃ fo...

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Abstract

The invention relates to the technical field of organic synthesis, and provides a preparation method of alpha-naphthylacetic acid. The invention aims to solve the problem that preparation of alpha-naphthylacetic acid is not economical and environmentally friendly in the prior art. The preparation method comprises the following steps: (1) dissolving naphthalene and Lewis acid in a solvent, carryingout heating, adding oxalyl chloride monoester, and carrying out a reaction to generate alpha-acetonaphthone acid ester; and (2) adding the alpha-acetonaphthone acid ester obtained in the step (1) andhydrazine hydrate into a high-boiling-point alcohol solvent, carrying out a heating reaction, adding a strong base, continuing the heating reaction, and adjusting a pH value to an acidic state afterthe reaction is finished so as to obtain alpha-naphthylacetic acid. According to the method, naphthalene and oxalyl chloride monoester which are cheap and easy to obtain are used as raw materials, alpha-acetonaphthone acid ester is prepared under the action of Lewis acid, and then a series of reactions are performed under the action of hydrazine hydrate to generate alpha-naphthylacetic acid, so the use of highly toxic cyanide is avoided, highly toxic or foul gas is not generated in the reaction process, only one product is produced, reaction conditions are mild, yield is high and cost is low.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of alpha-naphthaleneacetic acid. Background technique [0002] α-Naphthaleneacetic acid (α-Naphthalenelactic acid, molecular formula C 12 h 10 o 2 , CAS: 86-87-3), insoluble in water, safe and non-toxic to humans and animals, is a widely used plant growth regulator. α-naphthaleneacetic acid can promote the growth, flower preservation, fruit preservation and rooting of crops. Its main pharmacological functions are to promote plant cell division, enlargement, induce the formation of restless roots, increase fruit setting, promote metabolism and photosynthesis, and accelerate growth and development. [0003] The existing main synthesis methods of α-naphthaleneacetic acid are: ①Cyanide method. Naphthalene reacts with formaldehyde in hydrochloric acid system under the action of hydrogen chloride gas to generate chloromethylnaphthalene, which reacts ...

Claims

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Application Information

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IPC IPC(8): C07C51/02C07C57/40C07C51/00
CPCC07C51/02C07C51/00C07C249/16C07C67/343C07C57/40C07C251/86C07C69/738
Inventor 朱锦桃洪小平
Owner ZHEJIANG SCI-TECH UNIV
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