A kind of method for preparing benzoyl formate derivative

A technology of benzoyl formate and derivatives, which is applied in the field of preparation of benzoyl formate derivatives, can solve problems such as improper operation, low product yield, complicated operation, etc., and achieve mild conditions and good yield , the effect of simple operation

Active Publication Date: 2021-05-28
GUANGDONG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] 1. Grignard method, the Grignard reagent used in the Grignard method is more active, which makes the operation complicated. The reaction conditions are harsh and difficult to control. Improper operation is prone to multiple substitution reactions
[0005] 2. Catalytic oxidation method, the amount of potassium permanganate used in this process is large, the reaction is not easy to control, easy to produce by-products, and manganese-containing wastewater is not easy to treat, so it is not suitable for large-scale production
[0006] 3. Hydrolysis method, the process selectivity is poor, and the product yield is not high
[0007] 4. Friedel-Crafts acylation method, this reaction system requires high temperature resistance and corrosion resistance, the reaction time is too long, the energy consumption is large, and the production wastewater contains aluminum, so the post-treatment is complicated

Method used

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  • A kind of method for preparing benzoyl formate derivative
  • A kind of method for preparing benzoyl formate derivative
  • A kind of method for preparing benzoyl formate derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation method of embodiment 1 methyl benzoylformate

[0033] 54 mg (0.3 mmol) of alpha-methoxymethyl phenylacetate, 64 mg (0.36 mmol) of N-bromosuccinimide (NBS), were dissolved in 1 mL of ethyl acetate, and reacted for 1 hour under light conditions. After the reaction was completed, it was extracted three times with ethyl acetate, and the organic phases were combined and concentrated under reduced pressure. The crude product was separated and purified by silica gel column chromatography (diethyl ether: n-hexane = 1:50) to obtain 42 mg of a colorless liquid with a yield of 86%.

[0034] Under the same conditions, using alpha-hydroxyphenylacetic acid methyl ester as a raw material, the reaction yield of methyl benzoylformate was 80%.

[0035] Methyl benzoylformate:

[0036] 1 H NMR (400MHz, CDCl 3 )δ: 8.01 (dd, J=8.3, 1.1 Hz, 2H), 7.69–7.62 (m, 1H), 7.50 (t, J=7.8Hz, 2H), 3.97 (s, 3H).

[0037] 13 C NMR (100MHz, CDCl 3 )δ: 186.02, 164.02, 134.94, 132.42...

Embodiment 2

[0038] The preparation method of embodiment 2 m-chlorobenzoylformic acid methyl esters

[0039] 59.6 mg (0.3 mmol) of methyl 2-(3-chlorophenyl)-2-methoxyacetate, N-bromosuccinimide (NBS) (0.36 mmol), dissolved in 1 mL of ethyl acetate, in Under light conditions, react for 3 hours. After the reaction was completed, it was extracted three times with ethyl acetate, and the organic phases were combined and concentrated under reduced pressure. The crude product was separated and purified by silica gel column chromatography (diethyl ether: n-hexane = 1:50) to obtain 48 mg of white solid with a yield of 81%. Methyl m-chlorobenzoylformate:

[0040] 1 H NMR (400MHz, CDCl 3 )δ: 4.00(s, 3H), 7.47(t, J=7.9Hz, 1H), 7.64(dd, J=2.27, 7.9Hz, 1H), 7.93(d, J=8.1Hz, 1H), 8.03( s, 1H).

[0041] 13 C NMR (100MHz, CDCl 3 )δ: 53.0, 128.2, 129.8, 130.2, 133.9, 134.8, 135.2, 163.1, 184.4.

Embodiment 3

[0042] The preparation method of embodiment 3 p-chlorobenzoylformic acid methyl esters

[0043] 59.6 mg (0.3 mmol) of 2-(4-chlorophenyl)-2-methoxyacetic acid methyl ester, N-bromosuccinimide (NBS) (0.36 mmol), dissolved in 1 mL of ethyl acetate, in Under light conditions, react for 2 hours. After the reaction was completed, it was extracted three times with ethyl acetate, and the organic phases were combined and concentrated under reduced pressure. The crude product was separated and purified by silica gel column chromatography (diethyl ether: n-hexane = 1:50) to obtain 52 mg of a white solid with a yield of 87%.

[0044] Under the same conditions, using methyl 2-(4-chlorophenyl)-2-hydroxyacetate as a raw material, the yield of methyl benzoylformate was 90%.

[0045] Methyl p-chlorobenzoylformate:

[0046] 1 H NMR (400MHz, CDCl 3 )δ: 3.99 (s, 3H), 7.50 (d, J=8.5Hz, 2H), 8.00 (d, J=8.5Hz, 2H).

[0047] 13 C NMR (100MHz, CDCl 3 )δ: 52.9, 129.4, 130.8, 131.4, 141.7, 163...

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Abstract

The invention provides a method for preparing benzoyl formate derivatives, comprising dissolving alpha-methoxybenzoate or alpha-hydroxybenzoate and N-bromosuccinimide in an organic solvent , react under light conditions, and purify to obtain the benzoylformate derivative after the reaction is completed. The invention provides a novel method for preparing benzoylformate derivatives, which has simple operation, mild conditions and high yield.

Description

technical field [0001] The invention belongs to the technical field of synthetic chemistry, and more specifically relates to a method for preparing benzoylformate derivatives. Background technique [0002] Methyl benzoylformate, also known as methyl acetophenone, is a light yellow transparent liquid, soluble in solvents such as alcohol, ether, benzene and toluene, and hardly soluble in water. It is a kind of α-keto ester compound. It has more special chemical properties than ordinary compounds because it has both carbonyl and ester groups and many reaction centers. In addition, the carbonyl carbon in methyl benzoylformate is a potential chiral carbon, from which many chiral compounds with important uses can be synthesized, and it is an important intermediate in organic synthesis, which is widely used in pesticides, medicine, photoinitiation medicines and other fields. [0003] Methyl benzoylformate is as important organic synthesis intermediate, and the main synthetic meth...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/738C07C67/313
CPCC07C67/313C07C69/738
Inventor 丸岡啓二徐伟平柯翠连刘艳
Owner GUANGDONG UNIV OF TECH
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