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Method for preparing aliphatic alcohol at room temperature

A technology for aliphatic alcohols and aliphatic carboxylic acids, applied in hydrolysis preparation, chemical instruments and methods, preparation of hydroxyl compounds, etc., can solve the problem of high cost, and achieve the effects of short reaction time, wide application range and easy product post-processing

Active Publication Date: 2021-11-09
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, the existing method needs to use a catalyst that is difficult to synthesize, and the cost is high; on the other hand, the catalytic reaction requires 60 o The reaction temperature of C and the reaction time of 24 hours

Method used

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  • Method for preparing aliphatic alcohol at room temperature

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment one: Lithium anilide catalyzes the hydroboration reaction of acetic acid and pinacol borane

[0025] Under an inert gas atmosphere, add acetic acid (28.6 μl, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (290 μl, 2 mmol) with a pipette gun, and finally add 30 μL Tetrahydrofuran solution (0.1M) of anilinolithium (0.6 mol%, the same below), hydroboration reaction at room temperature for 55 minutes, and the reaction solution was exposed to air to obtain the product boric acid ester. , 0.5 mmol) as internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 The yield of H is 99%, when pinacol borane (218 microliters, 1.5 mmol), the yield is 96%; when pinacol borane (363 microliters, 2.5 mmol), the yield is 99%; the reaction time Be 30 minutes, yield 99%; The NMR data of product: 1 H NMR (400 MHz, CDCl 3 ): δ 3.86 (q, 2H, CH 2 ), 1.23 (s, 36H, CH 3 ), 1.20(br s, 3H, CH ...

Embodiment 2

[0027] Embodiment 2: Lithium anilide catalyzes the hydroboration reaction of valeric acid and pinacol borane

[0028] Under an inert gas atmosphere, add valeric acid (54.38 μl, 0.5 mmol) to the reaction flask after dehydration and deoxygenation, add pinacol borane (290 μl, 2 mmol) with a pipette gun, and finally add aniline Lithium (0.6 mol%) tetrahydrofuran solution, reacted at room temperature for 55 minutes, the reaction solution was exposed to air, and the solvent was removed to obtain the product borate, with s-trimethoxybenzene (84.12 mg, 0.5 mmol) as the internal standard , with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield was 92%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ): δ 3.80(t, 2H, OCH 2 ), 1.51-1.55 (m, 2H,CH 2 ), 1.29-1.51 (m, 4H, CH 2 ), 1.27(s, 36H, CH), 0.85(t, 3H, CH 3 ). Add 1g of silica gel and 2.5mL of methanol to the above hydroboration reaction after removing the solvent, and react at 50°C for 105 ...

Embodiment 3

[0029] Embodiment three: 4-Methoxyanilinide Lithium catalyzes the hydroboration reaction of hexanoic acid and pinacol borane

[0030]Under an inert gas atmosphere, add hexanoic acid (62.52 μl, 0.5 mmol) to the reaction flask after dehydration and deoxygenation, add pinacol borane (290 μl, 2 mmol) with a pipette gun, and finally add 4 - tetrahydrofuran solution of lithium methoxyanilinide (0.6 mol% dosage), reacted at room temperature for 55 minutes, exposed the reaction solution to air, and removed the solvent to obtain the product boric acid ester. mmol) as internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield was 90%. Replace 4-methoxyanilinidelithium with p-methylanilinidelithium, o-methylanilinidelithium, 2-methoxyanilinidelithium, anilinolithium, 2,6,-dimethylanilinidelithium, or 2,6-Diisopropylanilinide lithium, calculated product 1 The H yields were 91%, 90%, 93%, 90%, 91%, 92%, respectively. NMR data of the produ...

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Abstract

The invention relates to a method for preparing aliphatic alcohol at room temperature. The catalyst, borane and carboxylic acid are stirred and mixed in sequence, reacted for 50 to 60 minutes, exposed to the air to terminate the reaction, the reaction solution is decompressed to remove the solvent, and silica gel and methanol are added. , carry out the hydrolysis reaction to obtain aliphatic alcohols with different substituents. The anilinolithium compound disclosed in the present invention can catalyze the hydroboration reaction of carboxylic acid and borane with high activity at room temperature, and the amount of catalyst is only 0.6 mol% of the molar amount of carboxylic acid. Compared with the existing catalytic system, the use of A commercial reagent anilinolithium compound is developed, the reaction conditions are mild, and the yields of aliphatic alcohols with different substituents are high under limited conditions.

Description

technical field [0001] The technology for preparing organic alcohols involved in the present invention specifically relates to a method for preparing aliphatic alcohols at room temperature. Background technique [0002] The difference between carboxylic acid and aldehyde and ketone nucleophilic addition reaction activity: (1) The active hydrogen of carboxylic acid is easy to leave, so its two Os are actually equivalent, so from the perspective of space structure, the steric hindrance of carboxyl group is relatively small. Large, and the presence of carboxyl hydrogen bonds makes the electron cloud density of the entire carbonyl group larger, making it difficult for nucleophiles to attack the active center; (2) The nucleophile first attacks the carbonyl carbon, which is related to the electron cloud density on the carbon, the density Small ones attack first, for example, aldehydes and ketones have smaller electron cloud density than esters and amides, so they have high activit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/09C07C31/08C07C31/125C07C31/20
CPCC07C29/095C07F5/04C07C31/08C07C31/125C07C31/20
Inventor 薛明强康子晗徐晓娟颜丹丹洪玉标沈琪
Owner SUZHOU UNIV
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