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Method for preparing borate ester from fatty aldehyde

A technique for fatty aldehydes and boronate esters, applied in the field of preparing boronate esters, can solve the problems of weakening the nucleophilic addition activity of carbonyl, weakening the positive charge of carbonyl carbon, harsh reaction conditions, etc. The effect of adaptability and short reaction time

Inactive Publication Date: 2018-09-18
NANTONG TEXTILE & SILK IND TECH RES INST +1
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Problems solved by technology

However, in the catalytic systems reported so far, the catalysts are relatively expensive, or the reaction conditions are relatively harsh.
[0004] Although both belong to carbonyl compounds, ketones and aldehydes have different reaction properties. This is common knowledge. In the prior art, there are cases where ketones and aldehydes are used as raw materials at the same time but only one raw material reaction occurs; while the electron-donating group will weaken the positive charge of the carbonyl carbon. , thereby weakening the nucleophilic addition activity of the carbonyl group, aromatic aldehydes reduce the activity of the carbonyl group due to conjugation, so aromatic compounds with different substitution positions and different electronic effects have a large reaction difference with aliphatic compounds

Method used

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  • Method for preparing borate ester from fatty aldehyde
  • Method for preparing borate ester from fatty aldehyde
  • Method for preparing borate ester from fatty aldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: 2,6-Dimethylanilinolithium catalyzed the borohydride reaction of cyclohexylbenzaldehyde and pinacol borane

[0026] In a dehydrated and deoxygenated reaction flask, add 40 ul of 2,6-dimethylanilinolithium in tetrahydrofuran (0.05M) (0.2 mol% amount) under the protection of argon, and then add 0.1596 mL of borane with a syringe. Mix well, then add 0.095 mL 2-pyridinecarboxaldehyde with a syringe. The mixture is stirred at room temperature. After 10 minutes of reaction, the NMR yield is 99%. After that, a small amount of tetrahydrofuran and excess borane are removed under reduced pressure to obtain the corresponding pinnacle. Alcohol borate C 6 H 5 COCH 2 OB(OC(CH 3 ) 2 C(CH 3 ) 2 O). 1 H NMR (400 MHz, CDCl 3 ) δ 8.61 (d, J = 5.4 Hz, 1H, Ar-H), 7.91 (t, J = 7.7 Hz, 1H, Ar-H), 7.49-7.41 (m, 2H, Ar-H), 5.10 (s, 2H, OCH 2 ), 1.32 (s,12H, CH 3 ). 13 C NMR (101 MHz, CDCl 3 ) δ 159.82 (Ar-C), 143.72 (Ar-C), 139.56(Ar-C), 123.39 (Ar-C), 120.09 (Ar-C), 81.04 (OC), 66.47 (...

Embodiment 2

[0027] Example 2: 2,6-Dimethylanilinolithium catalyzed the borohydride reaction of propionaldehyde and pinacol borane

[0028] In a dehydrated and deoxygenated reaction flask, add 40 ul of 2,6-dimethylanilinolithium in tetrahydrofuran (0.05M) (0.2 mol% amount) under the protection of argon, and then add 0.1596 mL of borane with a syringe. Mix well, then add 0.072 mL propionaldehyde with a syringe. The mixture is stirred at room temperature. After 10 minutes of reaction, the NMR yield is 99%. After that, a small amount of tetrahydrofuran and excess borane are removed under reduced pressure to obtain the corresponding pinacol Borate CH 3 CH 2 COCH 2 OB(OC(CH 3 ) 2 C(CH 3 ) 2 O). 1 H NMR (400 MHz, CDCl 3 ) δ 3.80 (t, J = 6.6 Hz, 2H, OCH 2 ), 1.63-1.54(m, 2H, CH 2 ), 1.25 (s, 12H, CH 3 ), 0.91 (t, J = 7.4 Hz, 3H, CH 3 ). 13 C NMR (101MHz, CDCl 3 ) δ 82.04 (OC), 66.02 (OCH 2 ), 24.14 (CH 3 CH 2 ), 24.05 (CH 3 ), 9.55(CH 2 CH 3 ).

[0029] Substituting lithium 2,6-dimethylanilinide wit...

Embodiment 3

[0031] Example 3: 2,6-Dimethylanilinolithium catalyzes the borohydride reaction of n-heptanal and pinacol borane

[0032] In the reaction flask after dehydration and deoxygenation, add 40ul 2,6-dimethylanilinide lithium tetrahydrofuran solution (0.05M) (0.2 mol% amount) under the protection of argon, then add 0.1596 mL borane with a syringe, and mix well Then add 0.1392 mL n-heptanal with a syringe. The mixture is stirred at room temperature. After 10 minutes of reaction, the NMR yield is 99%. Then, a small amount of tetrahydrofuran and excess borane are removed under reduced pressure to obtain the corresponding pinacol boron. Ester C 6 H 13 COCH 2 OB(OC(CH 3 ) 2 C(CH 3 ) 2 O). 1 H NMR (400 MHz, CDCl 3 ) δ 3.82 (t, J = 8 Hz, 2H, OCH 2 ), 1.52-1.58 (m,2H, CH 2 ), 1.27-1.34 (m, 8H, CH 2 ), 1.24 (s, 12H, CH 3 ), 0.87 (t, J = 8 Hz, 3H,CH 3 ). 13 C NMR (100 MHz, CDCl 3 ) δ 82.02 (OC), 64.40 (OCH 2 ), 31.29 (CH 2 ), 30.92(CH 2 ), 28.44 (CH 2 ), 25.02 (CH 2 ), 24.00 (CH 3 ), 22.05 (CH ...

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Abstract

The invention relates to an application of lithium 2,6-dimethylamide, and concretely relates to a method for preparing borate ester by a hydroboration reaction of a fatty aldehyde and borane. The method comprises the following steps: adding borane into a reaction bottle subjected to dehydration and deoxidation treatment in an anhydrous oxygen-free environment in an inert gas atmosphere, adding a catalyst lithium 2,6-dimethylamide, uniformly mixing the borane with the catalyst, adding aldehyde, carrying out the hydroboration reaction, and exposing the reaction system to air to terminate the reaction in order to obtain the product borate ester, wherein the aldehyde is selected from fatty aldehyde. It is found that the lithium 2,6-dimethylamide can efficiently catalyze the hydroboration reaction of cyclohexylformaldehyde, propionaldehyde, n-heptanal and borane for the first time, so a new scheme is provided for the preparation of the borate ester by the hydroboration reaction of a carbonyl compound with borane.

Description

Technical field [0001] The invention relates to a method for preparing boric acid esters by utilizing the borohydride reaction of fatty aldehyde and borane. technical background [0002] The borate compound, the product of the borohydride reaction, can be used not only as a polymer additive, gasoline additive, flame retardant, sterilant, but also as a special surfactant, lubricant additive and automobile brake fluid, etc. Very extensive. It is also a very effective method to synthesize alcohols in contemporary organic synthetic chemistry to hydrolyze the obtained boric acid ester products for the hydrolysis of the equivalent catalyzed hydroboration of carbonyl compounds. Therefore, the research on the borohydride reaction of unsaturated bonds is of great significance to modern industry and synthetic organic chemistry, which has attracted widespread attention from scientific researchers. [0003] Various catalysts have been used for the hydroboration of aldehydes, especially in re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04B01J31/12
CPCC07F5/04B01J31/122
Inventor 薛明强朱章野洪玉标武振杰刘倩倩沈琪
Owner NANTONG TEXTILE & SILK IND TECH RES INST
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