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Preparation method of 2-acetoxyl-1,4-naphthoquinone

A technology of acetoxyl and naphthoquinone, applied in the field of preparation of naphthoquinone, can solve problems such as rare chemical properties

Inactive Publication Date: 2010-09-29
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 2-Hydroxy-1,4-naphthoquinone (HNQ) is a compound with a conjugated quinone structure, and there are few reports on its chemical properties
[0003] The acylation of hydroxyl group is a common reaction in organic synthesis. At present, more reports on this aspect are the acylation reaction of salicylic acid. In addition, there are reports on the synthesis method of 4-methyl-7-acetoxycoumarin , and utilize 2-hydroxy-1,4-naphthoquinone to prepare 2-acetoxy-1, the method for 4-naphthoquinone has not been reported yet

Method used

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  • Preparation method of 2-acetoxyl-1,4-naphthoquinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 7g of 2-hydroxy-1,4-naphthoquinone to 100mL of acetic anhydride; heat it in a water bath to 55°C and add concentrated sulfuric acid; react for 3 hours and cool the reactant to room temperature; add the reaction solution to 300mL of ice water and filter it to obtain 5.0 g of crude 2-acetoxy-1,4-naphthoquinone; add the crude product into 100 mL of ethyl acetate, heat until the solid dissolves, cool to room temperature, and filter with suction. The resulting product was baked in an oven at 50°C for 12 hours to dryness to obtain 4.5 g of the product with a yield of 80%, m.p.129°C.

Embodiment 2

[0019] Add 15g of 2-hydroxy-1,4-naphthoquinone to 200mL of acetic anhydride; heat it in a water bath to 55°C and add concentrated sulfuric acid; react for 5 hours and cool the reactant to room temperature; add the reaction solution to 300mL of ice water and filter it with suction to obtain 8.0 g of crude 2-acetoxy-1,4-naphthoquinone; add the crude product into 100 mL of ethyl acetate, heat until the solid dissolves, cool to room temperature, and filter with suction. The resulting product was baked in an oven at 50°C for 12 hours to dryness to obtain 7.2 g of the product with a yield of 72%, m.p.129°C.

Embodiment 3

[0021] Add 7g of 2-hydroxy-1,4-naphthoquinone to 100mL of acetic anhydride; heat in a water bath to 70°C and add concentrated sulfuric acid; react for 3 hours and cool the reactant to room temperature; add the reaction solution to 300mL of ice water and filter it to obtain 4.8g 2-acetoxy-1,4-naphthoquinone crude product; add the crude product into 100mL ethyl acetate, heat until the solid dissolves, cool to room temperature, and filter with suction. The obtained product was baked in an oven at 50°C for 12 hours until dry to obtain 4.0 g of the product with a yield of 81%, m.p.129°C.

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Abstract

The invention relates to a preparation method of 2-acetoxyl-1,4-naphthoquinone, comprising the following steps of: (A) adding 2- hydroxyl-1,4-naphthoquinone into acetic anhydride; (B) adding concentrated sulfuric acid under the condition of water bath heating; (C) cooling a reactant at normal temperature; (D) adding a reacting solution into cold water and carrying out suction filtering to obtain a 2-acetoxyl-1,4-naphthoquinone crude product; and (E) re-crystalizing by using an organic solvent. The method is simple and feasible; and the obtained product used as a pesticide has broad application prospect.

Description

technical field [0001] The invention relates to a preparation method of naphthoquinone, that is, a preparation method of 2-acetoxy-1,4-naphthoquinone. Background technique [0002] 2-Hydroxy-1,4-naphthoquinone (HNQ) is a compound with a conjugated quinone structure, and there are few reports on its chemical properties. HNQ is a green natural compound, which can react with acid anhydride to prepare antimalarial drugs. 2-Acetoxy-3-alkyl-1,4-naphthoquinone compounds have biological activity on organic matter and tissues such as bacteria, fungi, parasitic protozoa, insects, and 2-acetoxy-1, which has a similar structure, 4-Naphthoquinone has potential application as insecticide. [0003] The acylation of hydroxyl group is a common reaction in organic synthesis. At present, more reports on this aspect are the acylation reaction of salicylic acid. In addition, there are reports on the synthesis method of 4-methyl-7-acetoxycoumarin , and the method for preparing 2-acetoxy-1,4-na...

Claims

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Application Information

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IPC IPC(8): C07C69/157C07C67/08
Inventor 宋文华李丽颖
Owner TIANJIN POLYTECHNIC UNIV
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