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Method for preparing alcohol compound through uncatalyzed reaction of aromatic carboxylic acid

An aromatic carboxylic acid and alcohol compound technology, which is applied in the preparation of carboxylate, the preparation of organic compounds, and compounds containing elements of Group 3/13 of the periodic table, etc. High rate, wide application range, simple and controllable reaction process

Inactive Publication Date: 2019-04-05
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have obvious disadvantages: the LiAlH4 and NaBH4 systems have great safety risks, the SmI2-H2O-Et3N system requires a lot of excess reagents, and the transition metal complex system needs to be carried out under high temperature and high pressure.

Method used

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  • Method for preparing alcohol compound through uncatalyzed reaction of aromatic carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment one: pinacol borane and benzoic acid 3:1 mol ratio

[0021] Under an inert gas N2 atmosphere, add benzoic acid (61.1 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (218 μL, 1.5 mmol) with a pipette gun, and react at room temperature After 12 hours, the reaction was removed from the glove box, sampled, and NMR (with s-trimethoxybenzene (84.15 mg, 0.5 mmol) as the internal standard, dissolved in CDCl3, and stirred for 10 minutes), the calculated 1H yield was 99%, and the product NMR data: 1H NMR (400 MHz, CDCl3): δ 7.22– 7.32(m, 5H, ArH), 4.92 (s, 2H, CH2), 1.26 (s, 36H, CH3); add 1g to the sample residue Silica gel, using 3 mL of methanol as a solvent, reacted at 50 ° C for 3 h, further hydrolyzed the borate into alcohol, after the reaction, extracted three times with ethyl acetate, combined the organic layers, dried with anhydrous sodium sulfate, and removed the solvent under reduced pressure. Purificati...

Embodiment 2

[0022] Embodiment two: pinacol borane and benzoic acid 4:1 mol ratio

[0023] Under an inert gas N2 atmosphere, add benzoic acid (60.3 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (289 μL, 2 mmol) with a pipette gun, and react at room temperature After 6 hours, the reaction was removed from the glove box, and the reaction was completed to obtain boric acid ester, which was dissolved in CDCl3 with mes-trimethoxybenzene (83.05 mg, 0.5 mmol) as the internal standard, stirred for 10 minutes, sampled, and NMR. The 1H yield was calculated to be 90%. NMR data of the product: 1H NMR (400 MHz, CDCl3): δ 7.22– 7.32 (m, 5H, ArH), 4.92 (s, 2H, CH2), 1.26 (s, 36H, CH3). Add 1 g of silica gel to the sampling residue, use 3 mL of methanol as a solvent, and react at 50 ° C for 3 h to further hydrolyze the boric acid ester into alcohol. After the reaction, extract three times with ethyl acetate, combine the organic layers, and wash with...

Embodiment 3

[0024] Embodiment three: pinacol borane and benzoic acid 4:1 molar ratio

[0025] Under an inert gas N2 atmosphere, add benzoic acid (59.9 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (289 μL, 2 mmol) with a pipette gun, and react at room temperature After 12 hours, the reaction was removed from the glove box, and mes-trimethoxybenzene (82.50 mg, 0.5 mmol) was used as an internal standard, dissolved in CDCl3, stirred for 10 minutes, and sampled for NMR. The calculated 1H yield is 99%; NMR data of the product: 1H NMR (400 MHz, CDCl3): δ 7.22– 7.32 (m, 5H, ArH), 4.92 (s, 2H, CH2), 1.26 (s, 36H, CH3). Add 1 g of silica gel to the sampling residue, use 3 mL of methanol as a solvent, and react at 50 ° C for 3 h to further hydrolyze the boric acid ester into alcohol. After the reaction, extract three times with ethyl acetate, combine the organic layers, and wash with anhydrous sodium sulfate Dry, remove solvent under reduced...

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Abstract

The invention discloses a method for preparing alcohol compound through uncatalyzed reaction of aromatic carboxylic acid. The method includes: in an inert gas atmosphere, well stirring and mixing pinacolborane and carboxylic acid in a reaction bottle after dehydration deoxygenation, allowing reaction for 6-12h to obtain borate, and further hydrolyzing into alcohol, wherein the carboxylic acid is benzoic acid, 4-bromobenzoic acid, 4-fluorobenzoic acid, 1-naphthoic acid and 2-methoxybenzoic acid. The carboxylic acid is utilized to be in hydroboration reaction with borane efficiently in a catalyst-free condition for the first time, and a carbonyl compound is enabled to be in hydroboration reaction with borane to prepare borate which is further hydrolyzed into alcohol, in this way, a new scheme is provided.

Description

technical field [0001] The invention relates to the application field of green chemistry, in particular to a method for preparing alcohol compounds by reacting aromatic carboxylic acid and boric acid under the condition of no solvent and no catalyst. Background technique [0002] Alcohol is an important part of many synthetic transformations, drugs and materials synthesis, organoborates can be converted into alcohol under certain conditions. For the synthesis of borate esters, generally through the addition reaction of carbonyl compounds and boranes, the nucleophilic addition reactions of carboxylic acids and aldehydes and ketones are different: (1) the active hydrogen of carboxylic acids is easy to leave, so its two O It is actually equivalent, so from the perspective of the space structure, the steric hindrance of the carboxyl group is relatively large, and the presence of hydrogen bonds in the carboxyl group makes the electron cloud density of the entire carbonyl group la...

Claims

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Application Information

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IPC IPC(8): C07C33/22C07C29/09C07F5/04C07C33/46C07C43/23C07C41/26C07C33/18C07C33/24C07C33/20C07D209/12C07C65/01C07C51/367
CPCC07C29/095C07C41/26C07C51/367C07D209/12C07F5/04C07C33/22C07C33/46C07C33/18C07C33/24C07C33/20C07C43/23C07C65/01
Inventor 薛明强徐晓娟颜丹丹康子晗朱章野沈琪
Owner SUZHOU UNIV
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