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Method for synthesizing aromatic carboxylic ether by iodo aromatic hydrocarbon acarbonylation

A technology of aromatic carboxylic acid esters and iodoaromatics, which is applied in the field of halogenated benzene carbonylation to synthesize aromatic carboxylic acid ester compounds, can solve the problems of catalyst and product separation difficulties, loss of precious metals, pollution of phosphine compounds, etc., and achieve separation Easy, high reactivity, good selectivity

Inactive Publication Date: 2009-06-17
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology

However, in this type of reaction, a homogeneous phosphine-containing palladium catalyst system is usually used, and there are problems such as toxic phosphine compounds that will pollute the product, separation of the catalyst and the product, difficulty in reusing the catalyst, and loss of precious metals. These are difficult to overcome. Weakness has become a bottleneck restricting the application of oxo technology in the synthesis of aromatic carboxylic acids and derivatives

Method used

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  • Method for synthesizing aromatic carboxylic ether by iodo aromatic hydrocarbon acarbonylation

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Embodiment 1

[0028] 5%Pd / C: 5mg, Et 3 N: 7.2mmol, iodobenzene: 2.5mmol, anhydrous methanol 4mL, carbon monoxide pressure: 0.5MPa, react at 130°C for 2h to obtain methyl benzoate. The conversion rate of iodobenzene is 94%, and the selectivity of methyl benzoate is 100%.

Embodiment 2

[0030] With embodiment 1, used base is pyridine (7.2mmol), obtains methyl benzoate. The conversion rate of iodobenzene is 26%, and the selectivity of methyl benzoate is 100%.

Embodiment 3

[0032] With embodiment 1, do not add alkali, obtain methyl benzoate. The conversion rate of iodobenzene is 23%, and the selectivity of methyl benzoate is 100%.

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Abstract

The invention discloses a method for synthesizing aromatic carboxylic ester by carbonylation of aryl iodide. The method comprises: iodobenzene and derivatives of the iodobenzene, straight chain alcohol of C1 to C4 or phenolic compound and carbon monoxide are used as reactants to react in the presence of active carbon loaded palladium as a catalyst, an auxiliary catalyst and reaction solvent at 80 to 140 DEG C under a pressure of the carbon monoxide of between 0.1 and 2.5MPa for 0.5 to 8 hours, and obtaining the finished product. The method is highly efficient, economical and environment friendly, and has quite good industrial application prospect.

Description

technical field [0001] The invention relates to a method for synthesizing aromatic carboxylic acid ester compounds through the carbonylation of halogenated benzenes catalyzed by heterogeneous palladium catalysts under mild conditions. Background technique [0002] Aromatic carboxylate is a very important class of organic intermediates in industries such as chemical industry and pharmacy, and phenyl carboxylate is also widely used in the preparation of liquid crystal materials (reference: M.J.S.Dewer and P.S.Goldberg, J.Org.Chem. , 1974, 35, 3327) and the synthesis of biologically active compounds (reference: S. Neelakantan, R. Padmasani, T. R. Seshadri, Tetrahedron, 1965, 21, 3531). The carbonylation reaction of halogenated arenes is the main synthetic method of aromatic carboxylic acid esters ((a) Colguhoun, H.M.; Thompson, D.J.; Twigg, M.V.Carbonylation.Direct Synthesis of Carbonyl Compounds; Plenum Press: New York, 1991, ( b) Parshall, G.W.; Itell, S.D. Homogeneous Catal...

Claims

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Application Information

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IPC IPC(8): C07C67/36C07C69/76C07C69/78C07C69/773
Inventor 陈静刘建华夏春谷
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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