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Method for preparing beta, gama-unsaturated carboxylic acid compound
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A technology for compounds and carboxylic acids, applied in the field of compound synthesis, to achieve the effects of high yield, high conversion rate of reactants, and easy operation
Inactive Publication Date: 2017-11-10
UNIV OF SCI & TECH OF CHINA
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[0005] In view of this, the object of the present invention is to solve one or more problems or defects in the existing synthesis of β, γ-unsaturated carboxylic acid compounds
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[0045] Add tris(dibenzylidene indeneacetone)dipalladium (Pd 2 (dba) 3 , 0.5mol%, 2.3mg), 4,5-bisdiphenylphosphine-9,9-dimethylxanthene (xantphos, 2.0mol%, 5.8mg). The air in the tube was completely replaced with argon three times, and then 1 mL of toluene, cinnamyl alcohol (0.50 mmol, 67 mg), formic acid (1.5 mmol, 69 mg) and acetic anhydride (1.5 mmol, 152 mg) were added under an argonatmosphere. After the reaction tube was sealed, the reaction system was heated to 80°C in an oil bath and stirred continuously for 12 hours (IKA magnetic stirrer, RCT basic type, stirring speed 500 rpm). After the reaction was completed, the system was cooled to room temperature. The reaction solution was diluted with ethyl acetate, and then the diluted reaction solution was concentrated by rotary evaporation (BUCHI Co., ...
Embodiment 2
[0049] Example 2: Preparation of (E)-4-(4-methoxyphenyl)but-3-enoic acid
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Abstract
The invention provides a method for preparing a beta, gamma-unsaturated carboxylic acid compound. The method comprises the steps of making an allylic alcohol compound of a formula 1 or a formula 2 react with formic acid in the presence of a palladium catalyst, a phosphorous ligand, acid anhydride and an organic solvent to obtain the beta, gamma-unsaturated carboxylic acid compound of a formula 3 or formula 4, wherein R1, R2 and R3 are defined in the description. Formic acid is utilized as a carboxylationreagent, and the beta, gamma-unsaturated carboxylic acid compound is low in price, safe, stable and low in toxicity; the yield is high, the operation is simple, and the economy is high; compared with an existing compounding method, the use of toxic gascarbon monoxide and / or an equivalent quantity of reactive metal reagents is avoided, and the method meets requirements for environment-friendly chemistry; in addition, the dose of catalysts is small, the reaction condition is mild, the reactant is high in conversion rate and product yield, and the method has a very good industrial prospect.
Description
technical field [0001] The invention relates to the field of compound synthesis, in particular to a method for preparing β, γ-unsaturated carboxylic acid compounds by palladium-catalyzed reaction of formic acid and allyl alcohol. Background technique [0002] β,γ-unsaturated carboxylic acid compounds are very important intermediates in biomedicine, organic synthesis and chemical industry. [0003] About the synthetic method of β, γ-unsaturated carboxylic acid compounds, Ruth Naigre and Howard Alper's article (Palladium clay catalyzed regio-and stereospecific synthesis of β, γ-unsaturated acids by the carbonylation of allylic alcohols, Ruth Naigre and Howard Alper, Journal of The method disclosed in Molecular Catalysis A:Chemical 111 (1996) 11-15) utilizes carbon monoxide as carboxylationraw material, needs high carbonmonoxide pressure in its reaction system, and carbon monoxidetoxicity is big simultaneously, and operation is dangerous and difficult. [0004] In addition,...
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