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Carboxylic ester preparation method

A technology for synthesizing carboxylic acid esters and carboxylic acids, which is applied in the preparation of carboxylic acid esters, the preparation of carboxylic acid amides, the formation/introduction of carboxylic acid ester groups, etc. Large carboxylate, difficult to obtain and other problems, to achieve the effect of less environmental pollution, wide application range of substrates and simple reaction conditions

Inactive Publication Date: 2014-05-07
SICHUAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The route of traditional preparation carboxylate generally has two: the one, under acid catalysis, carboxylic acid and alcohol reaction generate ester (CN101024613A, CN102482192A, J.Org.Chem. 57 (1992) 6998-6999), this method is unfavorable for Generate acid-sensitive and sterically hindered carboxylates, although carboxylic acid derivatives (such as acid anhydrides, acid chlorides) can be reacted with alcohols to form esters, but acid anhydrides, acid chlorides, etc. need to be prepared additionally (formula a) The other is to use halogenated hydrocarbons, diazoalkane, dimethyl sulfate, etc. as alkylating reagents (formula b) (Org.Lett.1 (1999) 447-479, EP0757028A1, J. Org. Chem. 64 (1999)8014-8017), they have defects such as high toxicity, large environmental pollution, serious damage to equipment, poor selectivity or difficult access

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0023] Example 1 : Preparation of methyl p-nitrobenzoate

[0024]

[0025] Add 25 mmol of p-nitrobenzoic acid, 15 mmol of potassium carbonate and 50 ml of N,N-dimethylacetamide into the reaction flask, and o C for 0.5h. Then 37.5 mmol of methyl salicylate was added to continue the reaction for 20 h. After the reaction was completed, the solvent was evaporated under reduced pressure, an appropriate amount of water was added to the residue, and 12.5 mmol of potassium carbonate was added to hydrolyze the remaining methyl salicylate, which was detected by thin-layer chromatography. After the reaction is complete, extract with ethyl acetate, wash the organic phase with water and saturated sodium chloride, evaporate the solvent under reduced pressure to obtain the product carboxylate; The filter cake was solid; the filtrate was extracted with ethyl acetate, the organic phase was washed with water and saturated brine, and the solvent was evaporated under reduced pressure to ob...

Embodiment 2

[0026] Example 2 : Preparation of methyl o-methoxybenzoate

[0027]

[0028] Add 25 mmol of o-methoxybenzoic acid, 15 mmol of potassium carbonate and 50 ml of N,N-dimethylacetamide into the reaction flask, and o C for 0.5h. Then 37.5 mmol of methyl salicylate was added to continue the reaction for 24 h. After the reaction was completed, it was processed according to Example 1. Methyl p-nitrobenzoate yield 92%, 1 H NMR (600 MHz, CDCl 3 ) δ 7.80 (dd, J = 1.8, 7.8 Hz, 1H), 7.46-7.49 (m, 1H), 6.98-7.00 (m, 2H), 3.92 (s, 3H), 3.90 (s, 3H).

Embodiment 3

[0029] Example 3 : Preparation of methyl m-acetaminobenzoate

[0030]

[0031] Add 25 mmol of m-acetamidobenzoic acid, 15 mmol of potassium carbonate and 50 ml of N,N-dimethylacetamide into the reaction flask, at 110 o C for 0.5h. Then 37.5 mmol of methyl salicylate was added to continue the reaction for 20 h. After the reaction was completed, it was processed according to Example 1. The yield of methyl m-acetaminobenzoate is 86%. 1 H NMR (400 MHz, CDCl 3 ) δ 8.02 (s, 1H), 7.91 (d, J = 8.4 Hz, 1H), 7.78 (d, J = 7.6 Hz, 1H), 7.68 (br, 1H), 7.41 (t, J = 8.0 Hz, 1H), 3.90 (s, 3H), 2.21 (s, 3H).

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Abstract

The invention provides a method which is based on activation of salicylate intramolecular hydrogen bonds to prepare carboxylic ester through nucleophilic substitution reaction between salicylate used as an alkylating reagent and carboxylic acid anions. The method has the characteristics that the reagent is available at low cost and the salicylic acid is recyclable, the carboxylic ester is generated selectively by using carboxylic acid containing hydroxyl or amino groups, the reagent is small in toxicity, and less environmental pollution is caused.

Description

technical field [0001] The invention relates to a new method for preparing carboxylate. In the method, salicylate is used as an alkylating agent to undergo nucleophilic substitution reaction with carboxylic acid anions to prepare carboxylate. Background technique [0002] The preparation of carboxylic acid esters is a very important reaction in organic synthesis, and is widely used in the synthesis of drugs, food preservatives, spices and so on. The route of traditional preparation carboxylate generally has two: the one, under acid catalysis, carboxylic acid and alcohol reaction generate ester (CN101024613A, CN102482192A, J.Org.Chem. 57 (1992) 6998-6999), this method is unfavorable for Generate acid-sensitive and sterically hindered carboxylates, although carboxylic acid derivatives (such as acid anhydrides, acid chlorides) can be reacted with alcohols to form esters, but acid anhydrides, acid chlorides, etc. need to be prepared additionally (formula a) The other is to use ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/12C07C67/10C07C69/92C07C69/76C07C69/88C07C69/616C07C69/24C07C201/12C07C205/57C07C231/12C07C233/54C07C229/60C07C227/18C07D209/18C07D333/38
Inventor 罗美明陈思贾磊李笑男
Owner SICHUAN UNIV
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