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Method for synthesizing furan phenol by using aluminum dicarboxylate phenol as catalyst

A technology for catalyzing and catalyzing aluminum phenate dicarboxylate is applied in the field of preparation of furan phenol, and can solve the problems of not being able to control the reaction temperature and reduce the selectivity, so as to improve the selectivity of the cyclization reaction and improve the yield. efficient, easy to prepare

Inactive Publication Date: 2011-02-23
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The activation energy required for the Claisen rearrangement reaction is higher than the activation energy required for the Cope rearrangement. In the reaction of 2-(2-methallyloxy)phenol to prepare furanol by Claisen rearrangement, it is not possible to control the reaction temperature from the perspective of thermodynamics. Upper inhibition of Cope rearrangement or reduction of its selectivity

Method used

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  • Method for synthesizing furan phenol by using aluminum dicarboxylate phenol as catalyst
  • Method for synthesizing furan phenol by using aluminum dicarboxylate phenol as catalyst
  • Method for synthesizing furan phenol by using aluminum dicarboxylate phenol as catalyst

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Experimental program
Comparison scheme
Effect test

Embodiment 1 2

[0021] Embodiment 1 Diacetate aluminum phenate catalyzes the synthesis of furan phenol

[0022] (1) Preparation of Aluminum Diacetate Phenolate

[0023]

[0024] 20 mL of o-dichlorotoluene, 0.01 mol of aluminum isopropoxide and 0.01 mol of phenol, stirred at 35° C. for 1 h, rotary-evaporated to recover isopropanol, and cooled to obtain aluminum phenate diacetate.

[0025] (2) Catalytic synthesis of furanol with aluminum phenate diacetate

[0026]

[0027] 0.01mol aluminum phenate diacetate, 164g 2-(2-methallyloxy)phenol and 100mL o-dichlorobenzene were reacted at 180°C for 3.0h; after post-treatment, furan phenol was obtained in a yield of 82.6% (liquid chromatography, external standard, in terms of 2-(2-methylallyloxy)phenol, the same below).

Embodiment 2 2

[0028] Embodiment 2 2-methoxy phenol aluminum diacetate catalyzes the synthesis of furan phenol

[0029] (1) Preparation of 2-methoxy phenol aluminum diacetate

[0030]

[0031] 25 mL of N-methylpyrrolidone and toluene, 0.01 mol of aluminum isopropoxide acetate and 0.01 mol of 2-methoxyphenol, stirred at 40° C. for 1 h, rotary-evaporated to recover isopropanol, and cooled to obtain 2-methoxy phenolic aluminum diacetate.

[0032] (2) 2-Methoxy phenol aluminum diacetate catalyzed synthesis of furan phenol

[0033]

[0034] 0.01mol of 2-methoxyaluminum diacetate, 164g of 2-(2-methylallyloxy)phenol and 100mL of N-methylpyrrolidone were reacted at 165°C for 5.5h; after post-treatment, furanol was obtained with a yield of 82.3%.

Embodiment 3 2

[0035] Embodiment 3 2-naphthol aluminum diacetate catalyzes the synthesis of furanol

[0036] (1) Preparation of 2-naphthol aluminum diacetate

[0037]

[0038] 20 mL of xylene and diethylene glycol monomethyl ether, 0.01 mol of aluminum isopropoxide acetate and 0.01 mol of 2-naphthol, stirred at 35°C for 1 h, rotary-evaporated to recover isopropanol, and cooled to obtain 2-naphthol aluminum diacetate.

[0039] (2) 2-Naphthol aluminum diacetate catalyzed synthesis of furanol

[0040]

[0041] 0.01mol 2-naphthol aluminum diacetate, 164g 2-(2-methylallyloxy)phenol and 80mL diethylene glycol monomethyl ether were reacted at 180°C for 4.5h; after post-treatment, furan phenol was obtained with a yield of 82.0% .

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Abstract

The invention discloses a method for synthesizing furan phenol by using aluminum dicarboxylate phenol as a catalyst, which is to synthesize the furan phenol (1) under the catalytic action of the aluminum dicarboxylate phenol by using 2-(2-methylallyloxy)phenol as a raw material. The reaction equation is as follows: (RCO2)2AlOAr, wherein R may be C1 to C2 alkyl or C3 to C17 linear alkyl, branched alkyl or cycloalkyl; Ar may be phenyl, 2-methylphenyl, 4-methylphenyl, 2-methoxyphenyl, 4-methoxyphenyl, 2-ethyoxylphenyl, 4-ethyoxylphenyl, 2-phlorphenyl, 4-phlorphenyl, 2-carboxylphenyl, 2,6-dimethylphenyl, 2-biphenyl, 4-biphenyl, 1-naphthyl and 2-naphthyl. In the invention, furan phenol is synthesized by using aluminum dicarboxylate phenol as the catalyst, the raw material is readily available, production devices are not changed, the investment is small and quick in effectiveness, the furan phenol cyclization single-step yield is more than or equal to 81.0 percent, the furan phenol yield is much higher than that of the traditional process which uses aluminium isopropoxide as the catalyst, the production cost is reduced, and the economic benefit is obvious.

Description

technical field [0001] The invention relates to a preparation method of furan phenol (chemical name 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran), in particular to a method for catalyzing and synthesizing furan phenol by using aluminum dicarboxylate phenolate as a catalyst. Background technique [0002] Guan Aiguo et al. (CN1858309A) described the preparation methods of isopropoxy distearate aluminum and diisopropoxy stearoyl aluminum; studied isopropoxy distearate aluminum, diisopropoxy stearyl aluminum Application of acyl aluminum as additive in textile industry; Fenmans et al. (CN1832913A) described the preparation of aluminum diisopropoxide monoacrylate in solution; studied the application of aluminum diisopropoxide monoacrylate as additive in coating industry ; Japanese Patent (JP Laid-Open 2008138193A) describes aluminum diisopropoxide; studies the application of aluminum diisopropoxide in ink industry. Chinese patent (CN101402649) describes fatty acid aluminum isopro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/86B01J31/14
Inventor 陈平罗先福刘祈星
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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