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One-pot method for preparing 3-hydroxyphtalic anhydride

A technology of hydroxyphthalic anhydride and compounds, which is applied in the field of organic chemical synthesis, can solve the problems of complex process steps, difficult acquisition of raw materials, and low productivity, and achieve low equipment requirements, easy large-scale preparation, and mild conditions Effect

Inactive Publication Date: 2016-02-17
JINAN XUANHONG BIOLOGICAL PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Aiming at the problems of the prior art methods for preparing 3-hydroxyphthalic anhydride, such as complex process steps, low productivity, and difficult acquisition of raw materials, the present invention proposes a method utilizing 3-halogenated phthalic acid and esters thereof Derivative as raw material, efficient method for preparing 3-hydroxyphthalic anhydride

Method used

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  • One-pot method for preparing 3-hydroxyphtalic anhydride
  • One-pot method for preparing 3-hydroxyphtalic anhydride
  • One-pot method for preparing 3-hydroxyphtalic anhydride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 3-fluorophthalic acid (184.0g, 1.0mol) and N,N-dimethylformamide (600mL) in the three-necked flask, and start stirring; continue to add potassium hydroxide (112.2g, 2.0mol ) and cuprous iodide (5.7g, 0.03mol), the temperature was raised to 100°C for 6 hours of heat preservation reaction; TLC monitoring (methanol: dichloromethane=1:1, V / V) until the reaction was complete, cooled to room temperature, filtered ; The hydrochloric acid of 6.0mol / L of the filtrate is used to adjust the pH value between 1.0~2.0, and the filtrate is transferred to the there-necked flask, and under the situation of stirring, dicyclohexylcarbodiimide (722.2g, 3.5mol) is added and heated to Reaction at 100°C for 2 hours; TLC monitoring (methanol: dichloromethane = 1:1, V / V) until the reaction is complete, then lower to room temperature; extract with acetone (600mL×3), combine the organic phases, and wash with anhydrous sulfuric acid Dried over magnesium and filtered to obtain 162.3 g of off-wh...

Embodiment 2

[0029] Add 3-fluorophthalic acid (184.0g, 1.0mol) and cyclohexane (1100mL) in the three-necked flask, and start stirring; continue to add potassium tert-butoxide (336.6g, 3.0mol) and trifluoromethane during the reaction Copper sulfonate (18.1g, 0.05mol), heat up to 110°C and keep warm for 4 hours; TLC monitoring (methanol:dichloromethane=1:1, V / V) until the reaction is complete, cool down to room temperature, filter; filtrate Use 6.0mol / L hydrochloric acid to adjust the pH value between 1.0 and 2.0, transfer the filtrate to a three-neck flask, add dicyclohexylcarbodiimide (206.3g, 1.0mol) while stirring, and heat to 120°C Insulated reaction for 3.5 hours; TLC monitoring (methanol: dichloromethane = 1:1, V / V) until the reaction is complete, lowered to room temperature; extracted with methyl tert-butyl ether (1100mL × 3), combined organic phase, and used Dry over anhydrous magnesium sulfate and filter to obtain 154.4 g of 3-hydroxyphthalic anhydride off-white solid with a conver...

Embodiment 3

[0032] Add ethyl 3-fluorophthalate (240.0g, 1.0mol) and dimethyl sulfoxide (1000mL) in the there-necked flask, and start stirring; continue to add potassium tert-butoxide (336.6g, 3.0mol) in the reaction And cuprous iodide (2.0g, 0.01mol), heat up to 120°C and keep warm for 4 hours; TLC monitoring (methanol:dichloromethane=1:1, V / V) until the reaction is complete, cool down to room temperature, and filter; The filtrate was adjusted to a pH value between 1.0 and 2.0 with 6.0mol / L hydrochloric acid, and the filtrate was transferred to a three-necked flask. While stirring, dicyclohexylcarbodiimide (412.7g, 2.0mol) was added and heated to 130 ℃ for 2.5 hours; TLC monitoring (methanol: dichloromethane = 1:1, V / V) until the reaction is complete, then lowered to room temperature; extracted with ethyl acetate (1000mL × 3), combined organic phases, washed with anhydrous Dried over magnesium sulfate and filtered to obtain 210.2 g of off-white solid of 3-hydroxyphthalic anhydride, the co...

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Abstract

The invention relates to a one-pot method for preparing 3-hydroxyphtalic anhydride. The method comprises the following steps that a compound shown in a formula I is dissolved in organic solvent, and a reaction is conducted for 1-8 h at the temperature ranging from 80 DEG C to 130 DEG C under the alkaline condition in which a copper salt catalyst exists; then a condensing agent is added, and a reaction is conducted for 2-8 h at the temperature ranging from 100 DEG C to 130 DEG C; after purification is conducted through a purification agent, drying and filtration are conducted, and the 3-hydroxyphtalic anhydride is obtained. The method has the advantages of being short in synthetic route, mild in condition, easy to operate, high in yield and the like, and the HPLC purity can be made to be larger than or equal to 95 percent without complex post-treatment. The one-pot method for preparing the 3-hydroxyphtalic anhydride has great use value and social and economic benefits.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a method for preparing 3-hydroxyphthalic anhydride in one pot. Background technique [0002] 3-Hydroxyphthalic anhydride can be used as a raw material for heat-resistant resins such as epoxy resins, polyesters, and polyimides, or as a raw material for physiologically active substances such as medicines and pesticides. At present, there are not many synthetic methods of 3-hydroxyphthalic anhydride reported in literature and patents at home and abroad, and there are mainly the following three methods. [0003] Method 1: 2-hydroxybutyrate ketone and acetic anhydride in concentrated sulfuric acid to generate 2-oxo-2,5-dihydrofuran, 2-oxo-2,5-dihydrofuran in triethylamine, and Trimethylacetyl chloride reacts to generate 2-trimethylacetoxyfuran, and then the adduct of 2-trimethylacetoxyfuran and maleic anhydride is treated with concentrated sulfuric acid to obtain...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/89
CPCC07D307/89C07C51/56
Inventor 娄亚东李湛江刘彩云
Owner JINAN XUANHONG BIOLOGICAL PHARMA CO LTD
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