Preparation method for converting organic carboxylic acid into organic aldehyde

A technology of organic carboxylic acid and organic aldehyde, which is applied in the field of preparation of organic carboxylic acid into organic aldehyde, can solve the problems of low yield in the reaction process, industrial application limitations, and difficult handling, and achieve simple process, rapid reaction, tractable effect

Inactive Publication Date: 2008-12-10
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0003] HC Brown reported a two-step method for the preparation of aldehydes by reduction and oxidation of carboxylic acids (Synthesis, 1979). The disadvantage of this method is that pyridine-chromate, an expensive and highly toxic reagent, was used in the oxidation process. , and the post-treatment of the reaction product is difficult, the pollution is serious, and the yield of the whole reaction process is not high, which limits its industrial application

Method used

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  • Preparation method for converting organic carboxylic acid into organic aldehyde
  • Preparation method for converting organic carboxylic acid into organic aldehyde
  • Preparation method for converting organic carboxylic acid into organic aldehyde

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Embodiment 1

[0018] The preparation of n-octanal: 1) In a dry three-necked flask of 250ml, add n-octanoic acid 9.5ml (60mmol) and 100ml anhydrous ether, stir vigorously, add borane-dimethyl sulfide 6.12ml (60mmol) dropwise under normal temperature , Refluxed for 1 hour after the dropwise addition. Stop the reaction, remove anhydrous ether, and then add 50ml of acetone to obtain an acetone solution of the oxyboryl compound. 2) Add 0.01 g of TEMPO and 6.4 g of sodium carbonate to 50 ml of the acetone solution of the oxyboryl compound, and at 25° C., add dropwise 50 mL of the acetone solution of TCCA containing 5.1 g of TCCA (22 mmol) and stir; React for another 30 min, stop the reaction. Add water 30ml NH 4 The saturated aqueous solution of Cl was extracted three times with 150 ml of dichloromethane, dried, and the solvent was removed to obtain 7.4 g of the product with a yield of 96%.

Embodiment 2

[0020] The difference from Example 1 is that the preparation of 9-acyloxy n-nonanoic acid methyl ester: 12.1 g (60 mmol) of 9-methoxy-9-acyloxy n-nonanoic acid is dissolved in tetrahydrofuran solution, dropwise at room temperature Add 6.12ml (60mmol) of borane-dimethylsulfide, and then add 150ml of dichloromethane to obtain a dichloromethane solution of the oxyboryl compound. Then add 0.05g TEMPO and 5.8g pyridine, add dropwise 50ML acetone solution containing 5.6g TCCA at 0°C and stir for 60 minutes after the addition is complete, then stop the reaction. That is, the target product was obtained with a yield of 98%.

Embodiment 3

[0022] The difference from Example 1 is that the preparation of p-chlorobenzaldehyde: 9.4g (60mmol) of p-chlorobenzoic acid is dissolved in anhydrous ether solution, and 6.6ml (65mmol) borane-dimethyl sulfide is added dropwise at room temperature, Then add 50ml of acetone to obtain an acetone solution of the oxyboryl compound. Then add 0.02g TEMPO and 7.0g picoline, add dropwise 100ML acetone solution containing 6.0g TCCA at 5°C and stir, react for another 60min after the dropwise addition, and stop the reaction. That is, the target product was obtained with a yield of 96%.

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Abstract

The invention relates to organic synthesis, in particular to a preparation method for converting an organic carboxylic acid to an organic aldehyde. The method comprises the steps that: two reactions are carried out in a reaction container to convert a carboxyl in a carboxylic acid to a boroxyl compound first and then to oxidize theboroxyl compound to an aldehyde by an acetone solution of a trichloroisocyanuric acid with a mass 1.0 to 1.2 times that of the reaction substrate of carboxylic acid at a temperature of between 0 and 40 DEG C in the presence of 0.1 to 1.0 percent of 2,2,6,6-tetramethylpiperidine-1-oxyl against the mass of the reaction substrate of carboxylic acid and a base with a mass 1.0 to 1.2 times that of the reaction substrate of carboxylic acid. The method for preparing the aldehyde from the organic carboxylic acid by one-pot reaction of the invention has the advantages of moderate reaction conditions, rapid reaction, green reaction due to use of nontoxic oxidizer, simple process, easy operation, easy handling, and contribution to the realization of industrialization.

Description

technical field [0001] The invention relates to the synthesis of organic matter, in particular to a preparation method for converting organic carboxylic acid into organic aldehyde. Background technique [0002] Aldehyde is a very important compound in organic synthesis, and has important applications in petrochemical, fine chemical and pharmaceutical industries. In general, aldehydes are difficult to prepare by direct reduction of carboxylic acids because aldehydes are more easily reduced than carboxylic acids (Chemical Bulletin, 2002). [0003] HC Brown reported a two-step method for the preparation of aldehydes by reduction and oxidation of carboxylic acids (Synthesis, 1979). The disadvantage of this method is that pyridine-chromate, an expensive and highly toxic reagent, was used in the oxidation process. , and the post-treatment of the reaction product is difficult, the pollution is serious, and the yield of the whole reaction process is not high, so that its industrial...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/41C07C47/00
Inventor 夏传海刘莺杨翠云于君宝薛钦昭
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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