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N-butyl lithium based fatty alcohol preparation method

A technology of aliphatic alcohol and n-butyllithium, which is applied in the direction of hydrolysis preparation, chemical instruments and methods, and compounds containing elements of group 3/13 of the periodic table, etc., can solve the problem of high cost and achieve short reaction time and simple reaction Controllable, simple and controllable effect of the reaction process

Active Publication Date: 2019-04-19
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • N-butyl lithium based fatty alcohol preparation method
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: N-butyllithium 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 10 μL n-butyl Lithium tetrahydrofuran solution (0.1M) (0.2 mol% dosage, the same below), hydroboration reaction at room temperature for 15 minutes, the reaction solution was exposed to the air to obtain the product borate, with s-trimethoxybenzene (84.08 mg, 0.5 mmol) as internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 The yield of H was 99%, when pinacol borane (218 μL, 1.5 mmol), the yield was 95%; when pinacol borane (363 μL, 2.5 mmol), the yield was 99%; the NMR data of the product : 1 H NMR (400 MHz, CDCl 3 ): δ3.85(q, 2H, CH 2 ), 1.23 (s, 36H, CH 3 ), 1.21 (br s, 3H, CH 3 ). If n-butyllithium is r...

Embodiment 2

[0029] Example 2: n-Butyl Lithium Catalyzed Hydroboration Reaction of Valeric Acid and Pinacol Borane

[0030] Under an inert gas atmosphere, add valeric acid (54.38 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 n-butyl The tetrahydrofuran solution of lithium (0.2 mol% dosage) was reacted at room temperature for 15 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 93%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ): δ 3.81(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 1.1g of silica gel and 3mL of methanol to the above hydroboration reaction after removing the solvent, and rea...

Embodiment 3

[0031] Embodiment 3: n-Butyllithium catalyzes the hydroboration reaction of hexanoic acid and pinacol borane

[0032]Under an inert gas atmosphere, add hexanoic acid (62.52 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 4-formazol The tetrahydrofuran solution of oxyn-butyllithium (0.2mol% dosage) was reacted at room temperature for 15 minutes, and the reaction solution was exposed to air, and the solvent was removed to obtain the product borate, which was prepared in the form of s-trimethoxybenzene (84.01 mg, 0.5 mmol ) as internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield was 90%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ): δ 3.72 (t,2H,OCH 2 ), 1.45-1.51 (m, 2H,CH 2 ), 1.23-1.34 (m, 6H, CH 2 ), 1.17 (s, 48H, CH 3 ), 0.81 (t, 3H, CH 3 ). Add 1.1g of silica gel and 3mL of methanol to the above hydr...

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Abstract

The invention relates to an n-butyl lithium based fatty alcohol preparation method. In an inert gas atmosphere, borane and aliphatic carboxylic acid are mixed, then n-butyl lithium taken as the catalyst is added to carry out hydroboration reactions; and after the hydroboration reactions, silica gel and methanol are added to carry out hydrolysis reactions to obtain the fatty alcohols. N-butyl lithium can efficiently catalyze the hydroboration reactions between carboxylic acids and borane at a room temperature, the used catalyst only accounts for 0.2 mol% of the carboxylic acids, compared with aconventional catalyst system, a commercial catalyst namely n-butyl lithium is adopted, the reaction conditions are mild, and the yield of fatty alcohols with different substitutes under restricted conditions is high.

Description

technical field [0001] The technology for preparing organic alcohols involved in the present invention specifically relates to a method for preparing aliphatic alcohols based on n-butyllithium. Background technique [0002] Due to its stability and low toxicity, borate is widely used in various fields, and it is also the main raw material for the synthesis of alcohol compounds. 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 carb...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/12C07C31/08C07C31/125C07C31/20B01J31/12
CPCB01J31/122C07C29/12C07F5/04C07C31/08C07C31/125C07C31/20
Inventor 薛明强颜丹丹徐晓娟洪玉标刘倩倩沈琪
Owner SUZHOU UNIV
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